Diisopropylamine → HCID 87356133, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-bromothiophene (0.5 g, 3.00 mmol) in dry THF (5 mL) was cooled to −78° C. and freshly prepared lithium diisopropylamide (prepared from diisopropyl amine (0.5 mL, 3.60 mmol) and nBuLi (2.3 mL, 3.60 mmol, 1.6M in THF) was added dropwise. The reaction mixture was stirred at −78° C. for 1 h. Ethyl difluoro acetate (409 mg, 3.30 mmol) was added dropwise at −78° C. and the reaction mixture was stirred for 1 h, then slowly warmed up to room temperature and quenched with saturated NH4Cl solution. The organic product was extracted with EtOAc and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure to get 1-(5-bromothiophen-2-yl)-2,2-difluoroethanone (500 mg, yield 69%). 1H NMR (400 MHz, CDCl3) δ 7.77-7.75 (m, 1H), 7.21-7.20 (d, J=4.1 Hz, 1H), 6.27-6.00 (m, 1H).

Provenance & Evidence