Acetonitrile → HCID 86665624, compound

To a methylene chloride (50.0 mL) solution of 4-bromo-3-fluorobenzoic acid (5.00 g, 22.8 mmol), dimethylformamide (5 droplets) and oxalyl chloride (2.39 mL, 27.4 mmol) were added at room temperature, and the mixture was stirred for 1.5 hours at the same temperature. Subsequently, the solvent was distilled off under reduced pressure. The resulting residue was dissolved in tetrahydrofuran (15.0 mL)-acetonitrile (15.0 mL), and triethylamine (6.36 mL, 45.7 mmol) and a 2 M-trimethylsilyldiazomethane tetrahydrofuran solution (22.8 mL, 45.7 mmol) were added to the solution at room temperature. The mixture was stirred for 30 minutes. Water was added to the reaction mixture, and the mixture was subjected to extraction two times with ethyl acetate. The organic layer was washed with saturated brine, and then was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The resulting residue was washed with hexane-ethyl acetate (10:1, v/v). Thus, a crude product of the title compound (3.36 g) was obtained.

1. distillationSubsequently, the solvent was distilled off under reduced pressure
2. stirringThe mixture was stirred for 30 minutes
3. extractionthe mixture was subjected to extraction two times with ethyl acetate
4. washThe organic layer was washed with saturated brine
5. dry with materialwas dried over anhydrous sodium sulfate
6. distillationThe solvent was distilled off under reduced pressure
7. washThe resulting residue was washed with hexane-ethyl acetate (10:1

ORD record

ord-521755461e5846d4bd316ceab7267d27

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08557802B2