Dimethylformamide → Tert-butyl 4-bromo-3-methylbenzoate

4-Bromo-3-methylbenzoic acid (3.5 g, 16.27 mmol) was suspended in anhydrous dichloromethane (25 mL) under argon. DMF (0.5 mL) was added and followed by addition of oxalyl chloride (1.7 mL) at room temperature. The reaction mixture was stirred at room temperature for 20 min. and oxalyl chloride (0.5 mL) was added dropwise. The mixture was then stirred at room temperature for further 2 h. Solvent was evaporated. The residue was dissolved in anhydrous THF (25 mL) and cooled in an ice-bath. A solution of potassium tert-butoxide (3.65 g, 32.52 mmol) in anhydrous THF (20 mL) was added dropwise at 0° C. The reaction mixture was stirred at room temperature for 1 h, and water (100 mL) was added. The mixture was extracted with EtOAc and organic phase was washed with brine and water, and dried over anhydrous MgSO4. After evaporation of solvent, brown oil was obtained (3.78 g, 86%). MS (ESI) 272.76 (M+H+).

1. stirringThe mixture was then stirred at room temperature for further 2 h
2. customSolvent was evaporated
3. dissolutionThe residue was dissolved in anhydrous THF (25 mL)
4. temperaturecooled in an ice-bath
5. stirringThe reaction mixture was stirred at room temperature for 1 h
6. extractionThe mixture was extracted with EtOAc and organic phase
7. washwas washed with brine and water
8. dry with materialdried over anhydrous MgSO4
9. customAfter evaporation of solvent
10. custombrown oil was obtained (3.78 g, 86%)

ORD record

ord-01e5264329b84e7e9e7d2a24576bf64c

Source dataset

uspto-grants-2007_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07304085B2