4-Bromo-2-fluoroaniline → 3-Fluoro-3'-methoxy[1,1'-biphenyl]-4-amine

HRID 2360450Notes

Reaction equation

HRID 2360450 reaction equation
Br[C:2]1[CH:8]=[C:7]([F:9])[C:5]([NH2:6])=[CH:4][CH:3]=1.[CH3:10][O:11][C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=1>>[F:9][C:7]1[CH:8]=[C:2]([C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([O:11][CH3:10])[CH:17]=2)[CH:3]=[CH:4][C:5]=1[NH2:6]

Participants

3

Reactant 2

HCID 1230504-Bromo-2-fluoroanilineHCID 2734370(3-Methoxyphenyl)boronic acid

Product 1

HCID 201000673-Fluoro-3'-methoxy[1,1'-biphenyl]-4-amineYield 75.3%

Procedure

The title compound (430 mg) was prepared from 4-bromo-6-fluoroaniline (500 mg, 2.63 mmol) and 3-Methoxyphenylboronic acid (519 mg, 3.42 mmol) as a red liquid. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 7.34 (dd, J 2, 13.1, 1H), 7.27 (t, J 7.9, 1H), 7.22 (dd, J 2, 8.3, 1H), 7.12 (d, J 7.9, 1H), 7.09-7.07 (m, 1H), 6.84-6.78 (m, 2H), 5.29 (s, 2H), 3.78 (s, 3H).

Sources & evidence

ORD record
ord-1ce6c483bedd4f51b5be9e741d8ebf03
Source dataset
uspto-grants-2014_04
Patent number
US08686048B2

Reaction notes

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