4-Bromoaniline → HCID 91559901, compound

Participants

Reaction Conditions

Reaction Steps

A solution of tert.-Butyl hypochlorite (947 mg) in dichloromethane (15 mL) is added drop wise over a period of 1 h to a solution of trimethylene sulfide (0.63 mL) and 4-bromoaniline (1.50 g) in dichloromethane (60 mL) at −70° C. The reaction mixture is stirred for 15 min prior to the addition of a solution of 1,8-diazabycyclo[5.4.0]undec-7-ene (1.37 mL) in dichloromethane (10 mL). The reaction mixture is allowed to warm to −15° C. and quenched with water. The organic phase is separated, dried over MgSO4, and concentrated in vacuo. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 80:20-40:60) to give the title compound. LC (method 1): tR=1.16 min; Mass spectrum (ESI+): m/z=244, 246 [M+H]+.

Provenance & Evidence