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

HRID 1809325Notes

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

Sources & evidence

ORD record: ord-910bd3567a19452aa833832837d7b1b8
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362031B2

Reaction notes

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