* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Stage #1: With potassium <i>tert</i>-butylate In tetrahydrofuran at 0℃; for 0.0333333 h; Inert atmosphere Stage #2: With bromine In tetrahydrofuran at 20℃; for 0.0833333 h; Inert atmosphere
Under a nitrogen atmosphere, 2-nitrotoluene (2.00 g, 15.0 mmol) wa sdissolved in dry THF (90 mL), cooled to 0 °C, followed by addition of potassium t-butoxide. The reaction was stirred for 2 min before addition of bromine (3.12 g, 19.5 mmol). After further stirring for 5 min, the reaction was added to 500 mL of ice/water. The precipitate was filtered and the filtrate extracted with CH2Cl2 (3 × 100 mL). The combined organic layers were washed with saturated sodium thiosulfate solution and saturated sodium chloride solution, then dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by crystallization (H2O/EtOH, 1:2) to give 2,2′-dinitrodibenzyl as a white solid (1.94 g, 7.13 mmol, 95percent); mp 121 °C; Rf = 0.33 (n-pentane/CH2Cl2, 1:1). IR (ATR): 2962, 2854, 2343, 1608, 1576, 1509, 1443, 1344, 1310, 1262,1201, 1164, 1126, 1073, 1041, 959, 859, 787, 749, 704, 666, 567, 531, 421 cm–1. 1H NMR (500.1 MHz, CDCl3, 300 K): δ = 7.96 (dd, J = 8.2 Hz, J = 1.2 Hz,2 H, H-3), 7.54 (pseudo t, 2 H, H-5), 7.42 (dd, J = 7.7 Hz, J = 1.3 Hz, 2 H,H-6), 7.38 (pseudo t, 2 H, H-4), 3.25 (s, 4 H, CH2). 13C NMR (125.8 MHz, CDCl3, 300 K): δ = 149.37, 136.01, 133.30,132.49, 127.56, 124.84, 34.44. MS (EI, 70 eV): m/z (percent) = 273 (1) [M + H]+, 255 (8), 237 (9), 178 (21), 136 (100), 120 (70), 92 (85).
88%
With 5-chloro-1-methyl-1H-pyrazole-4-carbaldehyde; potassium hydroxide In N,N-dimethyl-formamide at 120℃; for 2 h; Inert atmosphere
3.46 mmol) and 2-nitrotoluene (1.42 g, 10.38 mmol) in DMF(4 mL) was treated with powdered KOH (388 mg, 6.92 mmol) andthen heated at 120 °C for 2 h. The resulting mixture was cooled tor.t. then treated with sat. aq NH4Cl (50 mL) and extracted withEtOAc (3 × 20 mL). The combined organic phases were washedwith brine (1 × 10 mL) and then dried (MgSO4), filtered, and concentratedunder reduced pressure to afford a yellow oil. The residuewas subjected to flash column chromatography (silica gel, EtOAc–hexane, 1:4 → 1:1 gradient elution) to afford two fractions, A and B.
Reference：
[1] Synthesis (Germany), 2017, vol. 49, # 15, p. 3471 - 3475
[2] Synthesis (Germany), 2013, vol. 45, # 23, p. 3211 - 3227
[3] Liebigs Annales, 1996, # 7, p. 1213 - 1216
[4] Journal of Organic Chemistry, 1942, vol. 7, p. 98,101
[5] Justus Liebigs Annalen der Chemie, 1948, vol. 559, p. 101,142
[6] Journal of the Chemical Society, 1901, vol. 79, p. 1276
[7] Journal of Organic Chemistry, 1979, vol. 44, # 25, p. 4705 - 4707
[8] Revue Roumaine de Chimie, 2009, vol. 54, # 11-12, p. 935 - 942
2
[ 577-19-5 ]
[ 69628-96-2 ]
[ 16968-19-7 ]
Yield
Reaction Conditions
Operation in experiment
72%
Stage #1: With iodine; magnesium In tetrahydrofuranHeating Stage #2: With dilithium tetrachlorocuprate In tetrahydrofuran at 55 - 60℃; for 10 h;
Into a reactor equipped with stirrer, heating device and reflux condenser was added o-nitrobromobenzene (II) (202g, 1.0 mol), tetrahydrofuran (2000g) and iodine (2.02g). After stirring evenly, add in batches polished magnesium chips (28.8g, 1.2 mol), then heat to micro-boiling until the reaction is initiated. then control the heating range. maintaining the reaction mixture at micro-boiling state until the magnesium disappears. The prepared o-nitrobromobenzene Gringard reagent is sealed for later use; In another reactor, add tetrahydrofuran (600g), lithium tetrachlorocuprate (101g) and p-toluenesulfonic acid o-nitrophenethyl ester (III) (321g, 1.0 mol). After stirring evenly, at room temperature add dropwise into the pre-prepared o-nitrobromobenzene Gringard reagent. Dropping temperature not more than 30 °C. After dropping, raise the temperature to 55-60 °C and continously stir the reaction for 10 hours; after the reaction by adding a small amount of dilute hydrochloric acid, filtered to remove insoluble matter, the filtrate is distilled under reduced pressure to remove the majority of the solvent, the obtained residue left standstill and separating solid, to obtain yellow powder, o-dinitrodibenzyl (I) crude, after isopropyl alcohol recrystallization, to obtain light yellow powder, o-dinitrodibenzyl (I) fine powder. 195.8g, yield about 72.0percent.
Reference：
[1] Patent: CN106749346, 2017, A, . Location in patent: Paragraph 0009; 0016; 0017; 0018
3
[ 88-72-2 ]
[ 16968-19-7 ]
[ 552-16-9 ]
Yield
Reaction Conditions
Operation in experiment
24%
With potassium hydroxide In methanol; water; anhydrous toluene (benzene)
Example 1 Preparation of 2,2'-dinitrobibenzyl A catalytic amount of a metal catalyst (0.01 g metal porfin or 0.005 g metal (AcAc)2 +0.01 g crown-ether) was added to a 33percent methanolic KOH-solution, (34 g KOH in 100 ml methanol). The reaction mixture was cooled to 25° C., 2-nitrotoluene (13.7 g, 0.1 mol) was added and air was passed through the reaction mixture, the temperature of the reaction mixture being kept at 25° C. After 12 hours the passsing through of air was interrupted and 150 ml water and 50 ml methanol was added. The reaction mixture was filtered. The filter layer was dissolved in boiling toluene (benzene), was filtered when hot, was cooled and was filtered again. Recrystallisation from ethanol gave a product with m.p. 120°-121° C. Yield 24-27percent. As a by-product o-nitrobenzoic acid was formed.
Reference：
[1] Patent: US4721821, 1988, A,
4
[ 612-23-7 ]
[ 16968-19-7 ]
Reference：
[1] Patent: CN107298645, 2017, A, . Location in patent: Paragraph 0020; 0022
5
[ 40754-26-5 ]
[ 16968-19-7 ]
[ 74808-60-9 ]
Reference：
[1] Journal of Organic Chemistry, 1980, vol. 45, # 23, p. 4597 - 4602
Reference：
[1] Journal of Organic Chemistry, 1980, vol. 45, # 23, p. 4597 - 4602
8
[ 103-29-7 ]
[ 16968-19-7 ]
[ 2220-30-6 ]
Reference：
[1] Rikagaku Kenkyusho Iho, 1942, vol. 21, p. 247[2] Scientific Papers of the Institute of Physical and Chemical Research (Japan), 1943, vol. 41, p. 182,189
[3] Scientific Papers of the Institute of Physical and Chemical Research (Japan), 1943, vol. 41, p. 182,188[4] Rikagaku Kenkyusho Iho, 1942, vol. 21, p. 247,249, 251
[5] Rikagaku Kenkyusho Iho, 1942, vol. 21, p. 247[6] Scientific Papers of the Institute of Physical and Chemical Research (Japan), 1943, vol. 41, p. 182,189
[7] , 1918, vol. 34 B, p. 175,183
[8] Scientific Papers of the Institute of Physical and Chemical Research (Japan), 1943, vol. 41, p. 182,188[9] Rikagaku Kenkyusho Iho, 1942, vol. 21, p. 247,249, 251
Reference：
[1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1997, # 7, p. 1265 - 1274
11
[ 103-29-7 ]
[ 16968-19-7 ]
[ 14310-29-3 ]
[ 6796-01-6 ]
[ 100-52-7 ]
Reference：
[1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1997, # 7, p. 1265 - 1274
12
[ 103-29-7 ]
[ 16968-19-7 ]
[ 14310-29-3 ]
[ 92085-83-1 ]
[ 100-52-7 ]
Reference：
[1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1997, # 7, p. 1265 - 1274
13
[ 1809-20-7 ]
[ 3958-60-9 ]
[ 16968-19-7 ]
[ 88-72-2 ]
Reference：
[1] Phosphorus, Sulfur and Silicon and the Related Elements, 1995, vol. 107, # 1-4, p. 33 - 48
14
[ 868-85-9 ]
[ 3958-60-9 ]
[ 16968-19-7 ]
[ 54006-08-5 ]
Reference：
[1] Phosphorus, Sulfur and Silicon and the Related Elements, 1995, vol. 107, # 1-4, p. 33 - 48
[2] Phosphorus, Sulfur and Silicon and the Related Elements, 1995, vol. 107, # 1-4, p. 33 - 48
15
[ 3958-60-9 ]
[ 16968-19-7 ]
[ 88-72-2 ]
Reference：
[1] Zeitschrift fuer Physikalische Chemie (Leipzig), 1989, vol. 270, # 2, p. 338 - 352
[2] Phosphorus, Sulfur and Silicon and the Related Elements, 1995, vol. 107, # 1-4, p. 33 - 48
[3] Zeitschrift fuer Physikalische Chemie (Leipzig), 1989, vol. 270, # 2, p. 338 - 352
[4] Catalysis Science and Technology, 2015, vol. 5, # 9, p. 4336 - 4340
16
[ 88-72-2 ]
[ 89-59-8 ]
[ 16968-19-7 ]
Reference：
[1] Bulletin de la Societe Chimique de France, 1972, p. 2444 - 2445
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