Dimethylformamide → HCID 13242431, compound

HRID 1649298Notes

Reaction equation

[CH:1]1[C:6]([C:7]([F:10])([F:9])[F:8])=[CH:5][C:4]([OH:11])=[CH:3][C:2]=1[C:12]([F:15])([F:14])[F:13].[OH-].[K+].CN(C)C=O.Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>C(OCC)C.O>[F:15][C:12]([F:13])([F:14])[C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([C:7]([F:9])([F:8])[F:10])[CH:1]=1)[O:11][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]

Participants

Conditions

Temperature: 25 °C

Procedure

To a stirred solution containing 11.5 g (0.05 mole) of 3,5-ditrifluoromethylphenol, 3.3 g (0.05 mole) of 85% potassium hydroxide, 200 ml of N,N-dimethylformamide and 10 ml of water, 0.055 mole of ethyl bromoacetate was added in one portion. The stirred reaction mixture was heated at 80°-90° C. for 46 hours. After cooling 25° C., 500 ml of water and 500 ml of ethyl ether were added; and stirring was continued for 15 minutes. The separated ether layer was washed with water until neutral to litmus and dried over sodium sulfate. The ether was removed in vacuo at a maximum temperature of 80°-90° C. at 1-2 mm of Hg. A product was obtained with ND25 of 1.4226 with a yield of 85%.

Workup

additionwas added in one portion
customThe stirred reaction mixture
temperaturewas heated at 80°-90° C. for 46 hours
washThe separated ether layer was washed with water until neutral to litmus and
dry with materialdried over sodium sulfate
customThe ether was removed in vacuo at a maximum temperature of 80°-90° C. at 1-2 mm of Hg
customA product was obtained with ND25 of 1.4226 with a yield of 85%

Sources & evidence

ORD record: ord-bafaac92c4d747b69e9c6862b22c57c2
Source dataset: uspto-grants-1983_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04416687

Reaction notes

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