2-Chlorophenylboronic acid → 2',3-Dichloro-5-fluorobiphenyl-4-amine

HRID 2360418Notes

Reaction equation

HRID 2360418 reaction equation
Br[C:2]1[CH:8]=[C:7]([F:9])[C:5]([NH2:6])=[C:4]([Cl:10])[CH:3]=1.[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B(O)O>>[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:2]1[CH:8]=[C:7]([F:9])[C:5]([NH2:6])=[C:4]([Cl:10])[CH:3]=1

Participants

3

Reactant 2

HCID 27343222-Chlorophenylboronic acidHCID 204346204-Bromo-2-chloro-6-fluoroaniline

Product 1

HCID 669972392',3-Dichloro-5-fluorobiphenyl-4-amineYield 42.3%

Procedure

The title compound (0.260 g) was prepared from 4-bromo-2-chloro-6-fluoroaniline (0.5 g, 2.4 mmol) and 2-chlorophenylboronic acid (0.453 g, 2.9 mmol) as a white solid. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 7.60 (d, J 7.3, 1H), 7.42-7.31 (m, 3H), 7.18-7.11 (m, 2H), 5.6 (s, 2H).

Sources & evidence

ORD record
ord-ccf17c0f7417460ca9f46f9141e34817
Source dataset
uspto-grants-2014_04
Patent number
US08686048B2

Reaction notes

Loading…