3-Fluoroaniline → [2-Chloro-4-(3-fluoro-phenylamino)-phenyl]-(2-methyl-5-nitro-phenyl)-methanone

HRID 2067280Notes

Reaction equation

HRID 2067280 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15](F)(F)[F:16])=C[CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:19]([C:21]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:22]=1[CH3:30])=[O:20].BrC1C=CC(C(C2C=C([N+]([O-])=O)C=CC=2C)=O)=C(Cl)C=1.FC1C=C(N)C=CC=1>>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:15]([F:16])[CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:19]([C:21]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:22]=1[CH3:30])=[O:20]

Participants

4

Reactant 3

HCID 97423-FluoroanilineHCID 11494123(4-Bromo-2-chloro-phenyl)-(2-methyl-5-nitro-phenyl)-methanoneHCID 68419760[2-Chloro-4-(4-trifluoromethyl-phenylamino)-phenyl]-(2-methyl-5-nitro-phenyl)-methanone

Product 1

HCID 68417015[2-Chloro-4-(3-fluoro-phenylamino)-phenyl]-(2-methyl-5-nitro-phenyl)-methanone

Procedure

The reaction was carried out similarly as described in the preparation of compound 414, using compound 402 (2.82 mmol) and 3-fluoro-phenylamine (2.82 mmol). The crude product was purified by continuous gradient flash chromatography using EtOAc/petroleum ether (40-60) 0:100 to 30:70 as the eluent to afford the title compound as yellow foam.

Workup

  1. customThe crude product was purified by continuous gradient flash chromatography

Sources & evidence

ORD record
ord-290075d1a3a64cf79f28fb48d072d035
Source dataset
uspto-grants-2012_10
Patent number
US08293772B2

Reaction notes

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