* 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.
General procedure: 2-Fluorobenzoyl chloride (6 mmol, 1.0 eq) in 2-methyltetrahydrofuran (15 mL) and Compound 2 (9 mmol,1.5 eq) of 2-methyltetrahydrofuran solution (15 mL) passed through material channels A and B, respectively, via metering pumps P1, P2.Mixing into a mixing module M having a preset temperature of 25 ° C at a flow rate of 1 mL/min,After staying in the reaction module L for 1 h,The reaction solution flows out from the outlet D.The reaction liquid flowing out from the outlet D was collected in a 1 mol/L hydrochloric acid solution.Quenched by stirring,Saturated saline solution,Dry over anhydrous sodium sulfate,Post-treatment by concentration, column chromatography, etc.Compound 5 was obtained.
Reference：
[1] Patent: CN108409516, 2018, A, . Location in patent: Paragraph 0049-0052
[2] Journal of the American Chemical Society, 1947, vol. 69, p. 662
2
[ 1765-93-1 ]
[ 446-52-6 ]
[ 342-25-6 ]
Yield
Reaction Conditions
Operation in experiment
98%
With potassium phosphate; palladium diacetate In water; methyl cyclohexane for 8 h; Reflux
Method of the present embodiment provides a 2,4 ′-difluorobenzophenone and preparation method thereof, as follows: in a 1000 ml round bottom flask The bottle was added sequentially o-fluoro benzaldehyde 124 g of 4-fluorophenylboronic acid and 140 g of potassium phosphate, 106 grams, 1.12 g of palladium acetate, then adding 500 ml of methyl cyclohexane and 100 ml of water and heated to reflux for 8 hours., sequentially passes through filtering, layering, washing with water, removing the solvent to obtain the product., 2,4 '-difluorobenzophenone 214 g, 98percent yield.
Reference：
[1] Tetrahedron Letters, 2009, vol. 50, # 4, p. 446 - 447
[2] Journal of the American Chemical Society, 1947, vol. 69, p. 662
[3] Russian Chemical Bulletin, 2001, vol. 50, # 7, p. 1208 - 1213
4
[ 462-06-6 ]
[ 403-43-0 ]
[ 345-71-1 ]
[ 342-25-6 ]
[ 345-92-6 ]
Reference：
[1] Chemical Communications, 2004, # 12, p. 1368 - 1369
5
[ 56-23-5 ]
[ 462-06-6 ]
[ 342-25-6 ]
[ 345-92-6 ]
Reference：
[1] Russian Chemical Bulletin, 2001, vol. 50, # 7, p. 1208 - 1213
With sodium tetrahydroborate; In ethanol; at 20℃; for 2h;
(1) (2-Fluorophenyl)(4-fluorophenyl)methanol To a solution (100 ML) of <strong>[342-25-6]2,4'-difluorobenzophenol</strong> (10.0 g, 45.8 mmol) in ethanol was added sodium borohydride (867 mg, 22.9 mmol), the mixture was stirred at room temperature for 2 hours, and the solvent was distilled off under reduced pressure.. The residue was poured into water, and was extracted with ethyl acetate.. The extracted solution was washed with water, was dried with anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure, to obtain the titled compound as oil. 9.88 g (97.8%) 1H-NMR (CDCl3) delta; 2.32 (1H, d, J = 4.0 Hz), 5.83 (1H, d, J = 4.0 Hz), 6.95 to 7.53 (8H, m)
EXAMPLE 5 The reaction was carried out as in Example 1 with the following compounds and under the following conditions: 19.2 g (yield: 88percent) of a mixture of raw 4,4'-difluoro- and 2,4'-difluorobenzophenone was recovered.
P.m.r. spectrum: (CDCl3 /TMS): 5.35 (1H: singlet); 5.63 (1H: singlet); 6.75-7.45 (8H: aromatic complex). The 2,4'-difluorobenzophenone used in this Example was obtained by a Friedel-Crafts reaction between fluorobenzene and 2-fluorobenzoyl chloride using an aluminium chloride catalyst.
...presented by the following formula (4) which can respectively correspond to the formula (1) can be obtained.(D) Fluorine substituted aromatic compound represented by the formula (4) corresponding to the hydroxy compound wherein X1 is a substituent of the group (a) in the formula(1):...4-trichloromethoxy-4'-fluorodiphenylether,4-methylsulfonyl-4'-fluorodiphenylether,4-phenylsulfonyl-4'-fluorodiphenylether,2,2'-difluorobenzophenone, 2,3'-difluorobenzophenone,2,4'-difluorobenzophenone, 3,3'-difluorobenzophenone,3,4'-difluorobenzophenone, 4,4'-difluorobenzophenone,4-methyl-4'-fluorobenzophenone, 4-methoxy-4'-fluorobenzophenone,4-phenyl-4'-fluorobenzophenone, 4-nitro-4'-fluorobenzophenone,...
9
[ 342-25-6 ]
[ 1745-81-9 ]
2,4'-bis[o-(1-propenyl)phenoxy]benzophenone[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With 1-methyl-pyrrolidin-2-one; potassium carbonate; In water; toluene;
EXAMPLE 10 Synthesis of 2,4'-bis[o-(1-propenyl)phenoxy]benzophenone o-Allylphenol (245.6 g), <strong>[342-25-6]2,4'-difluorobenzophenone</strong> (200 g), potassium carbonate (187.4 g), dry N-methylpyrrolidone (700 ml) and toluene (250 ml) are placed in a 3-necked 2500 ml flask fitted with a stirrer, reflex condensor and thermometer and the mixture is heated under nitrogen to a temperature of 160° C. and stirred for 8 hours. Water and toluene are separated via a Dean Stark trap and finally after 8 hours the reaction mixture reaches a temperature of 160° C. The mixture is cooled to 100° C. and a 1:1 mixture of toluene/water (1100 ml) is added while stirring. After phase separation the aqueous layer is washed with toluene (200 ml) and the combined toluene layers are washed 4 times with water (400 ml). The toluene phase is dried over sodium sulphate and toluene distilled off by use of a rotary evaporator finally in vacuum leaving 2,4'-bis[o-(1-propenyl)phenoxy]benzophenone as a light yellow melt. The yield is 396 g. The product has a melt viscosity of 350 mPa.s at 70° C.
1-(2-Fluorophenyl)-1-(4-fluorophenyl)-ethene[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
EXAMPLE 2 1-(2-fluorophenyl)-1-(4-fluorophenyl)ethene The procedure described in Example 1 is repeated except that the 130 parts of 2-chloro-4'-fluorobenzophenone are replaced by 168 parts of <strong>[342-25-6]2,4'-difluorobenzophenone</strong>, which was converted into the title compound in 85percent yield. Distillation, under vacuum, gives a colourless liquid which is pure 1-(2-fluorophenyl)-1-(4-fluorophenyl)ethene (b.pt. 82°/0.2 mm Hg). (Found: 77.7percent C; 4.6percent H; 17.5percent F; C14 H10 F2 requires: 77.8percent C; 4.7percent H; 17.6percent F).
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