2-Bromo-2-methylpropionyl bromide → 8-bromo-4-(2-fluorobenzenesulfonyl)-2,2-dimethyl-3,4-dihydro-2H-benzo[1,4]oxazine

HRID 388283Notes

Reaction equation

HRID 388283 reaction equation
[Br:1][C:2]1[C:11]2[O:10][C:9]([CH3:13])([CH3:12])[CH2:8][NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.BrC1C2OC(C)(C)C(=O)NC=2C=CC=1.NC1C=CC=C(Br)C=1O.BrC(C)(C)C(Br)=O.[F:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[S:51](Cl)(=[O:53])=[O:52]>>[Br:1][C:2]1[C:11]2[O:10][C:9]([CH3:13])([CH3:12])[CH2:8][N:7]([S:51]([C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=3[F:44])(=[O:53])=[O:52])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 886852-Bromo-2-methylpropionyl bromideHCID 1377612-Fluorobenzenesulphonyl chlorideHCID 155315062-Amino-6-bromophenolHCID 184491008-bromo-2,2-dimethyl-3,4-dihydro-2H-1,4-benzoxazineHCID 218735118-Bromo-2,2-dimethyl-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 225572828-bromo-4-(2-fluorobenzenesulfonyl)-2,2-dimethyl-3,4-dihydro-2H-benzo[1,4]oxazine

Procedure

Using the above procedure, but starting with 8-bromo-2,2-dimethyl-3,4-dihydro-2H-benzo[1,4]oxazine (prepared by reducing 8-bromo-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one, which in turn was prepared from 2-amino-6-bromophenol and 2-bromo-2-methylproprionyl bromide via the procedure described by Van Hes et al., WO 01/14330) and 2-fluorobenzenesulfonyl chloride, 8-bromo-4-(2-fluorobenzenesulfonyl)-2,2-dimethyl-3,4-dihydro-2H-benzo[1,4]oxazine was obtained as a white solid. MP.: 108.0-110.1°.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-a773888d5e7342fab340732ea0a8fbef
Source dataset
uspto-grants-2013_02
Patent number
US08377931B2

Reaction notes

Loading…