4-Fluoroaniline → HCID 178471928, compound

HRID 249294Notes

Reaction equation

HRID 249294 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[C:5]([C:10](=[O:20])[C:11]1[CH:16]=[C:15]([F:17])[C:14]([F:18])=[CH:13][C:12]=1[Cl:19])=[CH:6]OCC)[CH3:2].[F:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1>C(O)(C)C>[CH2:1]([O:3][C:4](=[O:21])[C:5]([C:10](=[O:20])[C:11]1[CH:16]=[C:15]([F:17])[C:14]([F:18])=[CH:13][C:12]=1[Cl:19])=[CH:6][NH:27][C:26]1[CH:28]=[CH:29][C:23]([F:22])=[CH:24][CH:25]=1)[CH3:2]

Participants

4

Reactant 2

HCID 97314-FluoroanilineHCID 54163438Ethyl 2-(2-chloro-4,5-difluorobenzoyl)-3-ethoxyacrylate

Product 1

HCID 178471928HCID 178471928, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2-(2-Chloro-4,5-difluorobenzoyl)-3-ethoxy-2-propenoic acid ethyl ester (material from preceding preparation) was mixed with isopropyl alcohol (250 ml) and cooled to 0°. 4-Fluoroaniline (9.33 g, 84.0 mmol) was added, and the reaction mixture was allowed to warm to room temperature and stir for 18 hours. The precipitate was filtered and washed with isopropyl ether, yielding the title product (11.0 g, 28.7 mmol). Additional product (10.2 g, 26.6 mmol, 73% overall yield for two steps) was obtained from the filtrate, which was concentrated in vacuo and subjected to column chromatography (eluting with chloroform), providing material was was further purified by recrystallization from ether/hexanes.

Workup

  1. temperaturecooled to 0°
  2. filtrationThe precipitate was filtered
  3. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-a31d664b18284ec8a1a6f00c79229818
Source dataset
uspto-grants-1993_05
Patent number
US05214051

Reaction notes

Loading…