N-bromobutanimide → 7-Bromo-6-hydroxy-1-heptanol
Reaction equation
[CH2:1]([OH:8])[CH2:2][CH2:3][CH2:4]CC=C.[Br:9]N1C(=O)CCC1=O.[C:17]([OH:21])(C)([CH3:19])[CH3:18].O>>[Br:9][CH2:18][CH:17]([OH:21])[CH2:19][CH2:4][CH2:3][CH2:2][CH2:1][OH:8]Participants
4
Procedure
To a solution of 3 (500 mg, 4.38 mmol) in t-butanol-water (24 mL-4 mL) in the dark was added N-bromosuccinimide (NBS) (858 mg, 4.82 mmol) in small portions. Additional NBS (312 mg) was added after 4 hours and 16 hours later another 400 mg of NBS was added. The reaction mixture was stirred for 68 hours. After removal of t-butanol in vacuo, the residue was diluted with ether, washed with saturated sodium thiosulfite solution, saturated sodium chloride solution, and dried over magnesium sulfate. The crude product was purified by HPLC to give 123 mg of 7-bromo-6-hydroxy-1-heptanol (4).