4-Bromo-2,6-dichloroaniline → HCID 66996798, compound

HRID 2360412Notes

Reaction equation

HRID 2360412 reaction equation
Br[C:2]1[CH:8]=[C:7]([Cl: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]([Cl:9])[C:5]=1[NH2:6]

Participants

3

Reactant 2

HCID 696804-Bromo-2,6-dichloroanilineHCID 27739203-Ethoxybenzeneboronic acid

Product 1

HCID 66996798HCID 66996798, compoundYield 88.6%

Procedure

The title compound (0.550 g) was prepared from 4-Bromo-2,6-dichloroaniline (0.5 g, 2.2 mmol) and 3-ethoxyphenylboronic acid (0.447 g, 2.7 mmol) as a yellow liquid which was about 70% pure as adjudged by 1H-NMR data. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 7.56 (s, 2H), 7.28 (s, 1H), 7.16-7.08 (m, 2H), 6.83 (dd, J 2, 8.1, 1H), 5.62 (s, 2H), 4.10 (q, J 7, 2H), 1.32 (t, J 7, 3H).

Sources & evidence

ORD record
ord-c056c92eccce4d6cb26a4e790343687c
Source dataset
uspto-grants-2014_04
Patent number
US08686048B2

Reaction notes

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