2-Bromophenyl isocyanate → SB705498
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]=[C:9]=[O:10].[F:11][C:12]([F:26])([F:25])[C:13]1[CH:14]=[CH:15][C:16]([N:19]2[CH2:23][CH2:22][C@@H:21]([NH2:24])[CH2:20]2)=[N:17][CH:18]=1>C(OCC)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:24][C@@H:21]1[CH2:22][CH2:23][N:19]([C:16]2[CH:15]=[CH:14][C:13]([C:12]([F:26])([F:25])[F:11])=[CH:18][N:17]=2)[CH2:20]1)=[O:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2-bromophenyl isocyanate (Aldrich Chemical Company) (27.4 ml, 0.222 mol) in dry diethyl ether (65 ml) was added dropwise over 0.5 h to an efficiently stirred solution of D2 (51.4 g, 0.222 mol) in dry diethyl ether (0.8 L) under argon at ambient temperature. After stirring for 18 h, a white precipitate was filtered off and washed with dry diethyl ether (2×150 ml). The solid was crushed to a fine powder and then re-stirred with diethyl ether (470 ml) for 4 h at ambient temperature. The insoluble product was filtered off, washed with diethyl ether (100 ml) and dried at 50° C./vacuum/24 h to afford title compound as a white solid.