4-Bromo-2,6-difluoroaniline → 3'-(Difluoromethoxy)-3,5-difluorobiphenyl-4-amine

HRID 2360427Notes

Reaction equation

HRID 2360427 reaction equation
Br[C:2]1[CH:8]=[C:7]([F:9])[C:5]([NH2:6])=[C:4]([F:10])[CH:3]=1.[F:11][CH:12]([F:23])[O:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1>>[F:11][CH:12]([F:23])[O:13][C:14]1[CH:19]=[C:18]([C:2]2[CH:8]=[C:7]([F:9])[C:5]([NH2:6])=[C:4]([F:10])[CH:3]=2)[CH:17]=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 6101914-Bromo-2,6-difluoroanilineHCID 177500693-(Difluoromethoxy)benzeneboronic acid

Product 1

HCID 669968223'-(Difluoromethoxy)-3,5-difluorobiphenyl-4-amineYield 55.3%

Procedure

The title compound (144 mg) was prepared from 4-bromo-2,6-difluoroaniline (200 mg, 0.96 mmol) and 3-(difluoromethoxy)phenylboronic acid (234 mg, 1.25 mmol) as a white solid. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 7.49 (d, J 7.9, 1H), 7.43-7.39 (m, 2H), 7.38-7.30 (m, 2H), 7.32 (t, J 74, 1H), 7.06 (dd, J 1.8, 7.9, 1H), 5.42 (s, 2H).

Sources & evidence

ORD record
ord-fb1802c5b38c43b1b73ed7c255d4d953
Source dataset
uspto-grants-2014_04
Patent number
US08686048B2

Reaction notes

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