(2H-1,3-benzodioxol-5-yl)boronic acid → 4-(Benzo[d][1,3]dioxol-5-yl)-2-chloro-6-fluoroaniline

HRID 2360431Notes

Reaction equation

HRID 2360431 reaction equation
Br[C:2]1[CH:8]=[C:7]([F:9])[C:5]([NH2:6])=[C:4]([Cl:10])[CH:3]=1.[O:11]1[C:15]2[CH:16]=[CH:17][C:18](B(O)O)=[CH:19][C:14]=2[O:13][CH2:12]1>>[O:11]1[C:15]2[CH:16]=[CH:17][C:18]([C:2]3[CH:8]=[C:7]([F:9])[C:5]([NH2:6])=[C:4]([Cl:10])[CH:3]=3)=[CH:19][C:14]=2[O:13][CH2:12]1

Participants

3

Reactant 2

HCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 204346204-Bromo-2-chloro-6-fluoroaniline

Product 1

HCID 669973834-(Benzo[d][1,3]dioxol-5-yl)-2-chloro-6-fluoroanilineYield 60.5%

Procedure

The title compound (143 mg) was prepared from 4-bromo-2-chloro-6-fluoroaniline (200 mg, 0.89 mmol) and benzo[d][1,3]dioxol-5-ylboronic acid (192 mg, 1.16 mmol) as a white solid. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 7.36-7.30 (m, 2H), 7.20 (d, J 1.7, 1H), 7.06 (dd, J 1.4, 8.1, 1H), 6.91 (d, J 8.1, 1H), 6.01 (s, 2H), 5.42 (s, 2H).

Sources & evidence

ORD record
ord-c255a8816c034c03881355e89c166097
Source dataset
uspto-grants-2014_04
Patent number
US08686048B2

Reaction notes

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