Sodium Carbonate → 4-Amino-6-bromo-5-hydroxy-2-methylbiphenyl-3-carbonitrile

HRID 17299Notes

Reaction equation

[NH2:1][C:2]1[C:7]([O:8]C)=[C:6]([Br:10])[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:4]([CH3:17])[C:3]=1[C:18]#[N:19].BrB(Br)Br.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.O>[NH2:1][C:2]1[C:7]([OH:8])=[C:6]([Br:10])[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:4]([CH3:17])[C:3]=1[C:18]#[N:19]

Participants

Conditions

Temperature: -70 °C

Procedure

4-Amino-6-bromo-5-methoxy-2-methylbiphenyl-3-carbonitrile (I-40) (44.5 mg, 0.14 mmol) was dissolved in dichloromethane (dewatered, 1.4 ml) under nitrogen atmosphere, and cooled in a dry ice-methanol bath at −70° C. 1 M Tribromoborane (dichloromethane solution, 0.42 ml) was dropwise added to it at −70 to −68° C., followed by stirring for 1.5 hours with heating up to 0° C. The reaction liquid was diluted with cold water, and controlled to have a pH of 6 to 7 with aqueous 10% sodium carbonate solution added thereto. The organic matter was extracted with ethyl acetate, washed with saturated brine, then dried on anhydrous magnesium sulfate, the solvent was evaporated away under reduced pressure to obtain the entitled compound (42.4 mg, quant.) as a pale brown solid.

Workup

temperaturewith heating up to 0° C
customThe reaction liquid
additionadded
extractionThe organic matter was extracted with ethyl acetate
washwashed with saturated brine
dry with materialdried on anhydrous magnesium sulfate
customthe solvent was evaporated away under reduced pressure
customto obtain the entitled compound (42.4 mg, quant.) as a pale brown solid

Sources & evidence

ORD record: ord-56883343fbf749ceb6d67d2ae4f68704
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Reaction notes

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