Dichloromethane → 4-Amino-3-cyano-6-fluoro-5-hydroxy-2-methylbiphenyl

HRID 17298Notes

Reaction equation

[F-].[F-].[F-].B.C(Cl)Cl.C(Cl)Cl.[NH2:11][C:12]1[C:17]([O:18]C)=[C:16]([F:20])[C:15]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:14]([CH3:27])[C:13]=1[C:28]#[N:29]>O>[NH2:11][C:12]1[C:17]([OH:18])=[C:16]([F:20])[C:15]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:14]([CH3:27])[C:13]=1[C:28]#[N:29]

Participants

Conditions

Temperature: 0 °C

Procedure

Under nitrogen atmosphere, at −78° C., 1 M borane trifluoride/methylene chloride solution (3.0 ml, 3.0 mmol) was dropwise added to a methylene chloride (10 ml) solution of 4-amino-3-cyano-6-fluoro-5-methoxy-2-methylbiphenyl (I-39) (250 mg, 1.0 mmol), taking 10 minutes, followed by stirring for 4 hours and a half with gradually heating up to 0° C. Water with ice was added to the reaction liquid, followed by neutralization at pH of 7 with aqueous 10% sodium carbonate solution and extraction three times with chloroform, the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate. After filtration and concentration under reduced pressure, the resulting residue gave the entitled compound (225 mg, 93%) as a white solid.

Workup

extractionfollowed by neutralization at pH of 7 with aqueous 10% sodium carbonate solution and extraction three times with chloroform
washthe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
filtrationAfter filtration and concentration under reduced pressure

Sources & evidence

ORD record: ord-65bd50426a9e487eb79916c044d4e82c
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Reaction notes

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