4-Fluoroaniline → [2-Chloro-4-(4-fluoro-phenylamino)-phenyl]-(2-methyl-5-nitro-phenyl)-methanone

HRID 2067223

Reaction equation

HRID 2067223 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2F)[CH:5]=[CH:4][C:3]=1[C:17]([C:19]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:20]=1[CH3:28])=[O:18].BrC1C=CC(C(C2C=C([N+]([O-])=O)C=CC=2C)=O)=C(Cl)C=1.FC1C=CC(N)=CC=1>>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:17]([C:19]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:20]=1[CH3:28])=[O:18]

Participants

4

Reactant 3

HCID 97314-FluoroanilineHCID 11494123(4-Bromo-2-chloro-phenyl)-(2-methyl-5-nitro-phenyl)-methanoneHCID 11618303[2-Chloro-4-(2,4-difluoro-phenylamino)-phenyl]-(2-methyl-5-nitro-phenyl)-methanone

Product 1

HCID 68419037[2-Chloro-4-(4-fluoro-phenylamino)-phenyl]-(2-methyl-5-nitro-phenyl)-methanone

Procedure

The reaction was carried out similarly as described in the preparation of compound 403, using compound 402 (22.6 mmol) and 4-fluoroaniline (24.8 mmol) except the time for the reaction was 16 h. The crude product was purified by flash chromatography using EtOAc/petroleum ether (40-60) 1:5 as the eluent to afford the title compound as yellow solid.

Workup

  1. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-66bc3954aef9491da07535f74576e44c
Source dataset
uspto-grants-2012_10
Patent number
US08293772B2

Linked notes

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