Dimethylformamide → 5-Bromo-2-methylbenzoyl chloride

5-Bromo-2-methylbenzoic acid (725 mg, 3.37 mmol, 1 eq) was suspended in dry dichloromethane (9.7 mL). Oxalyl chloride (0.32 mL, 3.74 mmol, 1.1 eq) and N,N-dimethylformamide (0.013 mL, 0.17 mmol, 0.05 eq) were then added at room temperature and the mixture was stirred for 6 hours. The solvent was then evaporated to give 5-bromo-2-methylbenzoyl chloride as yellow oil. This crude product was dissolved in dry dichloromethane (19.3 mL), AlCl3 (49.5 mg, 3.71 mmol, 1.1 eq) and 42 (600 mg, 3.37 mmol, 1 eq) were then added at 0° C. (internal temperature). The resultant mixture was stirred at this temperature for 30 minutes and then at room temperature overnight. The reaction mixture was poured into ice and water, the organic layer was separated and the aqueous layer was extracted with dichloromethane. The organic layers were gathered, dried over MgSO4, filtered and concentrated. The residue was taken up with n-hexane to form a precipitate which was collected by filtration, washed with n-hexane and dried to afford compound 43 (69% yield) as yellowish crystals.

1. customThe solvent was then evaporated

ORD record

ord-ca4f64c7107a45818099278a785b9695

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434670B2