Water → N-(5-Cyano-2-fluoro-3-hydroxy-6-methylbiphenyl-4-yl)-2,2-dimethylpropionamide

HRID 17322Notes

Reaction equation

ClCCl.[C:4]([C:6]1[C:7]([NH:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])=[C:8]([O:20]C)[C:9]([F:19])=[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:11]=1[CH3:12])#[N:5].BrB(Br)Br.O>[Cl-].[Na+].O>[C:4]([C:6]1[C:7]([NH:22][C:23](=[O:28])[C:24]([CH3:26])([CH3:25])[CH3:27])=[C:8]([OH:20])[C:9]([F:19])=[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:11]=1[CH3:12])#[N:5]

Participants

Conditions

Temperature: -78 °C

Procedure

A dichloromethane (60 ml) solution of N-(5-cyano-2-fluoro-3-methoxy-6-methylbiphenyl-4-yl)-2,2-dimethylpropionamide (I-70) (2.02 g, 5.93 mmol) was cooled at −78° C., a dichloromethane solution of 1 N tribromoborane (17.8 ml, 17.8 mmol) was dropwise added, followed by stirring at −78° C. for 15 minutes. Afterwards, this was heated up to −12° C., and stirred for 30 minutes. The reaction liquid was put into cold water (100 ml), saturated brine (50 ml) was added, the intended product was extracted with ethyl acetate (300 ml×2). The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1) to obtain the entitled compound (1.70 g, 88%) as a yellow solid.

Workup

temperatureAfterwards, this was heated up to −12° C.
stirringstirred for 30 minutes
customThe reaction liquid
additionwas added
extractionthe intended product was extracted with ethyl acetate (300 ml×2)
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record: ord-1927bafe632e4646ac4a4679308e61e9
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Reaction notes

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