2-Fluorophenylboronic acid → 3-Chloro-2',5-difluorobiphenyl-4-amine

HRID 2360411Notes

Reaction equation

HRID 2360411 reaction equation
Br[C:2]1[CH:8]=[C:7]([F:9])[C:5]([NH2:6])=[C:4]([Cl:10])[CH:3]=1.[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B(O)O>>[Cl:10][C:4]1[CH:3]=[C:2]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[F:11])[CH:8]=[C:7]([F:9])[C:5]=1[NH2:6]

Participants

3

Reactant 2

HCID 27343542-Fluorophenylboronic acidHCID 204346204-Bromo-2-chloro-6-fluoroaniline

Product 1

HCID 669976913-Chloro-2',5-difluorobiphenyl-4-amineYield 74.4%

Procedure

The title compound (0.392 g) was prepared from 4-bromo-2-chloro-6-fluoroaniline (0.5 g, 2.2 mmol) and 2-fluorophenylboronic acid (0.363 g, 2.6 mmol) as a pale-yellow liquid. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 7.51 (td, J 1.7, 7.8, 1H), 7.38-7.32 (m, 1H), 7.28 (s, 2H), 7.27-7.22 (m, 2H), 5.62 (s, 2H).

Sources & evidence

ORD record
ord-ad94376f70004c909e1f572e1dcd5986
Source dataset
uspto-grants-2014_04
Patent number
US08686048B2

Reaction notes

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