Dimethylformamide → HCID 18182333, compound

Reaction equation

[Br:1]N1C(=O)CCC1=O.CN(C)C=O.[CH2:14]([C:21]1[C:22]2[CH2:29][CH2:28][CH:27]([CH2:30][OH:31])[CH2:26][C:23]=2[S:24][CH:25]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O>[Br:1][C:25]1[S:24][C:23]2[CH2:26][CH:27]([CH2:30][OH:31])[CH2:28][CH2:29][C:22]=2[C:21]=1[CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

Procedure

103 mg of N-bromosuccinimide was added little by little to a solution of 5.0 ml of N,N-dimethylformamide containing 136 mg of 3-benzyl-6-(hydroxymethyl)-4,5,6,7-tetrahydrobenzo[b]thiophene under ice-cooling. After stirring for one hour, water was added to the reaction solution and the mixture was extracted with ethyl acetate. The organic phase was washed with water and brine, and the solvent was removed. Then, the residue was subjected to silica gel column chromatography and eluted with hexane and then with hexane/ethyl acetate (2:1), to give 164 mg of the target compound.