Dimethylformamide → HCID 13242428, compound

HRID 1649295Notes

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[CH:24]([CH3:30])[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][CH:24]([CH3:30])[C:25]([O:27][CH2:28][CH3:29])=[O:26]

Participants

Conditions

Temperature: 25 °C

Procedure

To a stirred solution containing 17.3 g (0.075 mole) of 3,5-ditrifluoromethylphenol, 5 g (0.075 mole) of 85% potassium hydroxide, 150 ml of dimethylformamide and 7 ml of water, 14.6 g (0.08 mole) of ethyl 2-bromopropionate was added in one portion. The stirred reaction mixture was heated at 80°-90° C. for 24 hours. After cooling to 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 maximum temperature of 50°C. at 1-2 mm of Hg. The resulting product was obtained as an amber liquid, ND25 =1.4184 in 97% yield.

Workup

additionwas added in one portion
customThe stirred reaction mixture
temperaturewas heated at 80°-90° C. for 24 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 maximum temperature of 50°C. at 1-2 mm of Hg
customThe resulting product was obtained as an amber liquid, ND25 =1.4184 in 97% yield

Sources & evidence

ORD record: ord-98154d984bd246049fa05c7ca7af3097
Source dataset: uspto-grants-1983_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04416687

Reaction notes

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