Water → Methyl 2-(2-nitro-4-(trifluoromethyl)phenyl)acetate

HRID 388622Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:22])[CH:4]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:10]=1[N+:19]([O-:21])=[O:20])C(OC)=O.[Cl-].[Na+].O>CS(C)=O>[CH3:1][O:2][C:3](=[O:22])[CH2:4][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:10]=1[N+:19]([O-:21])=[O:20]

Participants

Conditions

Temperature: 120 °C

Procedure

2-(2-Nitro-4-trifluoromethylphenyl)-malonic acid dimethyl ester (68 g, 0.21 mol) was dissolved in dimethyl sulfoxide (200 mL). Sodium chloride (34 g, 0.58 mol) and water (60 mL) were added and the mixture was stirred for 16-20 h at 120° C. (reaction monitored by TLC). The reaction mixture was then cooled to room temperature and quenched into water, which caused precipitation of the product. After stirring for 30 minutes, the product. (45 g, 80%) was isolated by filtration. The product was used without further purification in the next reaction. A small sample was crystallized (EtOAc/hexane, 2:8) for analysis, to yield yellow crystals, mp 104-105° C. 1H NMR (CDCl3) 8.3 (s, 1H), 7.88 (d, J=8.4 Hz, 1H), 7.50 (d, J=8.4 Hz, 1H), 4.12 (s, 2H), 3.60 (s, 3H). MS (FAB) m/z: 275.2 (M++1).

Workup

custom(reaction monitored by TLC)
temperatureThe reaction mixture was then cooled to room temperature
customquenched into water, which
customprecipitation of the product
stirringAfter stirring for 30 minutes
custom(45 g, 80%) was isolated by filtration
customThe product was used without further purification in the next reaction
customA small sample was crystallized (EtOAc/hexane, 2:8) for analysis
customto yield yellow crystals, mp 104-105° C

Sources & evidence

ORD record: ord-980dbeea74934c869152bdc20e9429a5
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08377958B2

Reaction notes

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