4-Bromo-2-fluoroaniline → 3-Fluoro-3′-(trifluoromethoxy)[1,1′-biphenyl]-4-amine

HRID 2360413Notes

Reaction equation

HRID 2360413 reaction equation
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.[F:10][C:11]([F:23])([F:22])[O:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1>>[F:9][C:4]1[CH:3]=[C:2]([C:15]2[CH:16]=[CH:17][CH:18]=[C:13]([O:12][C:11]([F:10])([F:22])[F:23])[CH:14]=2)[CH:8]=[CH:7][C:5]=1[NH2:6]

Participants

3

Reactant 2

HCID 1230504-Bromo-2-fluoroanilineHCID 27343853-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride)

Product 1

HCID 551313313-Fluoro-3′-(trifluoromethoxy)[1,1′-biphenyl]-4-amineYield 34.8%

Procedure

The title compound (0.5 g) was prepared from 4-Bromo-2-fluoroaniline (1 g, 5.3 mmol) and 3-(trifluoromethoxy)phenylboronic acid (1.4 g, 6.8 mmol) as a yellow liquid. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 7.62 (d, J 8, 1H), 7.53 (s, 1H), 7.48 (t, J 8, 1H), 7.42 (dd, J 2, 9.1, 1H), 7.28 (dd, J 2, 8.3, 1H), 7.23 (d, J 11, 1H), 6.82 (t, J 8.5, 1H), 5.40 (s, 2H).

Sources & evidence

ORD record
ord-e5b8b6b84afa4c51b93fb62b086708e0
Source dataset
uspto-grants-2014_04
Patent number
US08686048B2

Reaction notes

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