Chlorosulfamic acid → 2-(4-Bromophenyl)ethyl sulfamate

Reaction equation

[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1.[H-].[Na+].[S:13](Cl)(=[O:16])(=[O:15])[NH2:14]>CN(C=O)C>[S:13](=[O:16])(=[O:15])([O:8][CH2:7][CH2:6][C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][CH:4]=1)[NH2:14]

Participants

Procedure

A mixture of 2.95 g (0.015 mole) of 4-bromophenethyl alcohol in 10 ml DMF was added dropwise to a suspension of sodium hydride 0.90 g, 60% in oil; 0.065 mole) in 35 ml DMF at 0°-5° C. The suspension was stirred for 20 min under argon after which sulfamoyl chloride (2.09 g, 0.018 mole) was added portionwise at 0°-5° C. After stirring for 20 min, the resultant suspension was poured into ice and extracted twice with Et2O. The combined organic phases were washed with saturated brine, dried over potassium carbonate and concentrated in vacuo to a white solid which was recrystallized in EtOAc/hexane to give 2.40 g (59%) of the title compound as a white solid, mf 109°-110° C.