Ethanol → Methyl 4-[4-(2-trifluoromethylphenyl)-2-oxazolyl]benzoate

HRID 1264924Notes

Reaction equation

[C:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[NH2:2].[F:14][C:15]([F:27])([F:26])[C:16]1[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=1[C:18](=O)[CH2:19]Br.CN(C)C=O.C(O)C>O>[F:14][C:15]([F:26])([F:27])[C:16]1[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=1[C:18]1[N:2]=[C:1]([C:4]2[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=2)[O:3][CH:19]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of methyl 4-carbamoylbenzoate (896 mg), 2-trifluoromethylphenacyl bromide (2.22 g) and N,N-dimethylformamide (5 ml) was stirred at 130° C. for 2 hours. Hot ethanol was added to the reaction mixture, which was poured into water, and extracted with ethyl acetate. The ethyl acetate layer was concentrated, and the residue was subjected to a silica gel column chromatography to obtain methyl 4-[4-(2-trifluoromethylphenyl)-2-oxazolyl]benzoate as an oil from a fraction eluted with ethyl acetate-hexane. This oil was dissolved in a mixture of tetrahydrofuran (10 ml) and ethanol (10 ml), and hydrolyzed by adding a 1N aqueous solution of sodium hydroxide (10 ml). The reaction mixture was neutralized with 1N hydrochloric acid, and precipitated crystals were collected by filtration. The product was recrystallized from acetone-hexane to obtain 4-[4-(2-trifluoromethylphenyl)-2-oxazolyl]benzoic acid (203 mg, yield: 12%). Colorless prisms. Melting Point: 264 to 265° C.

Workup

extractionextracted with ethyl acetate
concentrationThe ethyl acetate layer was concentrated

Sources & evidence

ORD record: ord-8fc333006682418499c65efc042a9e92
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06545009B1

Reaction notes

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