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CAS No. : | 1345847-71-3 | MDL No. : | MFCD27939981 |
Formula : | C12H12FNO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BQEDPQDMNWOYLK-UHFFFAOYSA-N |
M.W : | 237.23 | Pubchem ID : | 66598761 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | A solution of 4-fluoroaniline (1.11g, 10 mmol) and NaOMe (0.54 g, 10 mmol) in toluene (12 mL) was stirred under Ar at 100 °C (bath temperature), and the MeOH/toluene azeotrop was distilled off at 63 °C. In a stream of Ar, toluene (2mL) was distilled to ensure complete removal of MeOH. To this mixture, <strong>[6914-71-2]dimethyl 1,1-cyclopropanedicarboxylate</strong> (1.58 g, 10 mmol) in toluene (5 mL) was added, and the heating was continued. Again, the MeOH/toluene azeotrop was distilled off, followed by toluene in a stream of Ar at a slightly higher bath temperature. The residue was allowed to cool and was stirred with H2O (10 mL) and HCl (10 mL 1M), then extracted with CH2Cl2 (10 mL). The organic phase was dried over MgSO4 and evaporated. The residue was repeatedly extracted with i-pentane (12 × 10 mL). The solvent was removed under reduced pressure at 50 °C to yield the crystalline product (1.32 g, 56percent); mp 76 °C; IR (neat): 1705,1659, 1550, 1506, 1443, 1205, 1151, 838, 716 cm?1; 1H NMR (300 MHz, DMSO-d6) delta 1.38?1.42 (m, 4H),3.68 (s, 3H), 7.11?7.17 (m, 2H), 7.60?7.65 (m, 2H), 10.34 (1H); 13C NMR (75 MHz, DMSO-d6) delta 16.3(2C), 29.8, 52.4, 115.2 (d, J = 22.5 Hz, 2C), 121.1 (d, J = 7.9 Hz, 2C), 135.4, 158.1 (d, J = 239.6 Hz),165.8, 171.8; HRMS (FAB) m/z 238.1128 (calcd 238.0874 for C12H13FNO3, [M+H]+). Single-crystal diffraction: T = 173(2) K; thetamax = 67.4°; CuKalpha radiation; indices ?15 ? h ? 10, ?8 ? k ? 5, ?14 ? l ? 13; Dx= 1.42 g cm?3; 3313 reflections measured, 1077 independent with Rint = 0.026, F(000) = 496, mu = 0.97mm?1. Crystal data for 4, C12H12FNO3 (M = 237.23 g mol?1): orthorhombic, Pnma, a = 13.026(1), b =6.998(1), c = 12.139(1) A, V = 1106.63(11) A3, Z = 4. R1 = 0.036 and wR2 = 0.102 for 903 reflections withI > 2sigma(I), R1 = 0.043 and wR2 = 0.108 for all data; S = 1.06; Deltarhomax = 0.19 and Deltarhomin = ?0.18 e A?3. CCDCreference number 1419002. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91.3% | With sodium hexamethyldisilazane; In tetrahydrofuran; at 0 - 20℃; for 2h; | Dimethyl 1,1-cyclopropyldicarboxylate (10.9 g, 0.069 mol, 1.0 eq.),p-Fluoroaniline (11.6 g, 0.104 mol, 1.5 eq.) was added to 100 mL of tetrahydrofuran, and the temperature was lowered to 0 C.2M bis(trimethylsilyl)amide sodium (NaHMDS) / tetrahydrofuran (207 mL, 0.414 mol, 6.0 eq.) was added with stirring.The reaction was stirred at room temperature for 2 h.At the end of the reaction, 1.8 L of purified water was added, stirred and crystallized for 5-6 h, filtered, and 20 mL of filter cake purified water was washed.Methyl 1-((4-fluorophenyl)carbamoyl)cyclopropanecarboxylate13.7 g, yield 91.3%, purity 99.7%. |
56% | 4-Fluoraniline (1.11 g, 10 mmol) was dissolved in toluene (12 mL), sodium methoxide (0.54 g,10 mmol) were added. Then the mixture was stirred 30 minutes under inert atmospherewherein the bath temperature was raised from 80 to 100 00 and about 2 mL of azeotropic methanol/toluene mixture was evaporated. Next, dimethyl cyclopropane-1,1-dicarboxylate (1.58 g, 10 mmol) in toluene (5 mL) was added and azetropic distillation under stirring and inert gas flow was continued for another 30 minutes. Upon cooling to room temperature water (10 mL) and iN hydrochloric acid (10 mL 1M) were added, the mixture was stirred for 10minutes and extracted with dichloromethane (10 mL). The organic layer was dried over magnesium sulfate und the solvent was evaporated. The residue (2.07 g) was extracted withiso-pentane (12x10 mL) Evaporation of the solvent provided 1.32 g (56%) of the crystalline title compound (m.p.: 76 00). |