4-Bromo-2,6-difluoroaniline → 3,5-Difluoro-3′-methoxy[1,1′-biphenyl]-4-amine

HRID 2360400Notes

Reaction equation

HRID 2360400 reaction equation
[F:1][C:2]1[CH:8]=[C:7](Br)[CH:6]=[C:5]([F:10])[C:3]=1[NH2:4].[CH3:11][O:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1>>[F:1][C:2]1[CH:8]=[C:7]([C:17]2[CH:16]=[CH:15][CH:14]=[C:13]([O:12][CH3:11])[CH:18]=2)[CH:6]=[C:5]([F:10])[C:3]=1[NH2:4]

Participants

3

Reactant 2

HCID 6101914-Bromo-2,6-difluoroanilineHCID 2734370(3-Methoxyphenyl)boronic acid

Product 1

HCID 533754393,5-Difluoro-3′-methoxy[1,1′-biphenyl]-4-amineYield 79.6%

Procedure

The title compound (992 mg) was prepared from 2,6-difluoro-4-bromo aniline (1.1 g, 5.3 mmol) and 3-methoxyphenylboronic acid (1.04 g, 6.8 mmol) as a pale-yellow liquid. 1H-NMR (δ ppm, CDCl3+DMSO-d6, 400 MHz): 7.21-7.20 (m, 1H), 6.99-6.89 (m, 3H), 6.87-6.83 (m, 1H), 6.74-6.68 (m, 1H), 3.97 (bs, 2H), 3.69 (s, 3H).

Sources & evidence

ORD record
ord-f515b2c10644440db27dd84e1f5c20b9
Source dataset
uspto-grants-2014_04
Patent number
US08686048B2

Reaction notes

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