Water → N-(3-Bromo-6-cyano-2-hydroxy-5-methyl-4-styrylphenyl)-2,2-dimethylpropionamide

HRID 17274

Reaction equation

ClCCl.[Br:4][C:5]1[C:6]([O:29]C)=[C:7]([NH:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[C:8]([C:20]#[N:21])=[C:9]([CH3:19])[C:10]=1[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.BrB(Br)Br.O>[Cl-].[Na+].O>[Br:4][C:5]1[C:6]([OH:29])=[C:7]([NH:22][C:23](=[O:28])[C:24]([CH3:25])([CH3:27])[CH3:26])[C:8]([C:20]#[N:21])=[C:9]([CH3:19])[C:10]=1[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A dichloromethane (1.0 ml) solution of N-(3-bromo-6-cyano-2-methoxy-5-methyl-4-styrylphenyl)-2,2-dimethylpropionamide (I-11) (34 mg, 79.6 μmol) was cooled at −78° C., a dichloromethane solution of 1 N tribromoborane (239 μl, 239 μmol) was dropwise added, followed by stirring at −78° C. for 70 minutes. Afterwards, this was heated up to −12° C. and stirred for 1 hour. The reaction liquid was put into cold water (50 ml), saturated brine (50 ml) was added, the intended product was extracted with ethyl acetate (50 ml×2). The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure to obtain the entitled compound (32 mg, 96%) as a yellow white semi-solid.

Workup

temperatureAfterwards, this was heated up to −12° C.
stirringstirred for 1 hour
customThe reaction liquid
additionwas added
extractionthe intended product was extracted with ethyl acetate (50 ml×2)
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-8c67044626f3465faa6208c6c8d738ae
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Linked notes

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