4-Bromo-3-chloroaniline → (E)-Ethyl 3-(4-amino-2-chlorophenyl)-2-butenoate

HRID 2265100Notes

Reaction equation

HRID 2265100 reaction equation
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[Cl:9].[C:10]([O:15][CH2:16][CH3:17])(=[O:14])/[CH:11]=[CH:12]/[CH3:13].NC1C(F)=CC(/C(/C)=C/C(OCC)=O)=C(F)C=1>>[NH2:6][C:5]1[CH:7]=[CH:8][C:2](/[C:12](/[CH3:13])=[CH:11]/[C:10]([O:15][CH2:16][CH3:17])=[O:14])=[C:3]([Cl:9])[CH:4]=1

Participants

4

Reactant 3

HCID 888884-Bromo-3-chloroanilineHCID 429065Ethyl trans-crotonateHCID 86644278(E)-Ethyl 3-(4-amino-2,5-difluorophenyl)-2-butenoate

Product 1

HCID 86644282(E)-Ethyl 3-(4-amino-2-chlorophenyl)-2-butenoateYield 31%

Procedure

Using 4-bromo-3-chloroaniline (10.0 g) and ethyl crotonate (10.0 ml), Compound 12a (3.56 g, 31%) was obtained as a brown solid in the same manner as Compound 10a was synthesized.

Sources & evidence

ORD record
ord-91d8c67f60aa45309e8e81ba4677388e
Source dataset
uspto-grants-2010_12
Patent number
US07855300B2

Reaction notes

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