3-Ethoxybenzeneboronic acid → 3-Chloro-3'-ethoxy-5-fluorobiphenyl-4-amine

HRID 2360408Notes

Reaction equation

HRID 2360408 reaction equation
Br[C:2]1[CH:8]=[C:7]([F:9])[C:5]([NH2:6])=[C:4]([Cl:10])[CH:3]=1.[CH2:11]([O:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1)[CH3:12]>>[Cl:10][C:4]1[CH:3]=[C:2]([C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([O:13][CH2:11][CH3:12])[CH:19]=2)[CH:8]=[C:7]([F:9])[C:5]=1[NH2:6]

Participants

3

Reactant 2

HCID 27739203-Ethoxybenzeneboronic acidHCID 204346204-Bromo-2-chloro-6-fluoroaniline

Product 1

HCID 669977763-Chloro-3'-ethoxy-5-fluorobiphenyl-4-amineYield 67.7%

Procedure

The title compound (0.360 g) was prepared from 4-bromo-2-chloro-6-fluoroaniline (0.5 g, 2.0 mmol) and 3-ethoxyphenylboronic acid (0.441 g, 2.65 mmol) as a yellow liquid. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 7.43-7.38 (m, 2H), 7.27 (t, J 7.9, 1H), 7.14 (d, J 7.9, 1H), 7.10 (s, 1H), 6.82 (dd, J 2.1, 8.1, 1H), 5.51 (s, 2H), 4.07 (q, J 7, 2H), 1.32 (t, J 7, 3H).

Sources & evidence

ORD record
ord-728fe857a8bd4fdab3c6c37a027ac9fd
Source dataset
uspto-grants-2014_04
Patent number
US08686048B2

Reaction notes

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