1,1,1,3-Tetrabromopropan-2-one → 2,4-Dibromo-6-cyclopropyl-8-(4-(trifluoromethyl)phenylsulfonyl)-8-azabicyclo[3.2.1]oct-6-en-3-one

Participants

Reaction Steps

Diethyl zinc (18.1 mL, 18.1 mmol of a 1M solution in hexane) was added to a solution of 3-cyclopropyl-1-(4-(trifluoromethyl)phenylsulfonyl)-1H-pyrrole (3.18 g, 10.1 mmol) and tetrabromoacetone (7.53 g, 20.1 mmol) in toluene at −10° C. The reaction mixture was stirred at room temperature for 17 h and was subsequently diluted with EtOAc and washed with saturated aqueous Na2CO3. The organic phase was separated, dried (Na2SO4), filtered, concentrated under vacuum and purified on a silica gel column (eluant hexane/EtOAc, 9/1 to 7/3, v/v) to give compound 115 (3.31 g, 6.25 mmol, 62%). MS (ESI) 530.0 (M+H).

Provenance & Evidence