Water → HCID 11481595, compound

Participants

Reaction Steps

To a stirred solution of n-butyllithium 1.6 M in hexanes (17.5 mL, 28.1 mmol) was added at −20° C. under argon 2,2,6,6-tetramethylpiperidine (4.7 mL, 28.1 mmol) in anhydrous THF (40 mL). After cooling (−50° C.), 3-bromobenzoic acid (2.54 g, 12.8 mmol) in anhydrous THF (10 mL) was added dropwise and the mixture was stirred for 1 h. The mixture was then treated with an excess of DMF (3.7 g, 50.4 mmol). The resulting solution was allowed to warm up to ambient temperature, after which water was added. The aqueous layer was washed with diethyl ether, and then acidified with 4M HCl. The mixture was diluted with diethyl ether and the organic layer was separated and dried with MgSO4. The residue was purified by crystallization using with EtOAc/PE to give the crude title product (1.18 g, yield: 41%).

Provenance & Evidence