4-Bromo-2,6-difluoroaniline → 3,5-Difluoro-3'-propoxybiphenyl-4-amine

HRID 2360417Notes

Reaction equation

HRID 2360417 reaction equation
Br[C:2]1[CH:8]=[C:7]([F:9])[C:5]([NH2:6])=[C:4]([F:10])[CH:3]=1.[CH2:11]([O:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1)[CH2:12][CH3:13]>>[F:10][C:4]1[CH:3]=[C:2]([C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([O:14][CH2:11][CH2:12][CH3:13])[CH:20]=2)[CH:8]=[C:7]([F:9])[C:5]=1[NH2:6]

Participants

3

Reactant 2

HCID 6101914-Bromo-2,6-difluoroanilineHCID 3691230(3-Propoxyphenyl)boronic acid

Product 1

HCID 669971653,5-Difluoro-3'-propoxybiphenyl-4-amineYield 47.5%

Procedure

The title compound (0.3 g) was prepared from 4-Bromo-2,6-difluoro aniline (0.5 g, 2.4 mmol) and 3-propoxyphenylboronic acid (0.337 g, 3.1 mmol) as a red liquid. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 7.30-7.24 (m, 3H), 7.18-7.10 (m, 2H), 6.86-6.80 (m, 1H), 5.31 (s, 2H), 3.97 (t, J 6.5, 2H), 1.75-1.65 (m, 2H), 0.98 (t, J 7.4, 3H).

Sources & evidence

ORD record
ord-b234d6b9f0a2428294c6fb83114474fd
Source dataset
uspto-grants-2014_04
Patent number
US08686048B2

Reaction notes

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