Ethyl 2-(3,4-difluorophenyl)-2-oxoacetate → Ethyl 3,3',4,4'-tetrafluorobenzilate

HRID 49173Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:9](=[O:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][C:7]=1[F:8]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[F:8])[C:9]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[C:7]([F:8])[CH:6]=1)([OH:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

Conditions

Temperature: 5 °C

Procedure

The Grignard reagent is prepared from 2.24 g (0.092 mol) of magnesium chips, a few granules of iodine and 17.80 g (0.092 mol) of 1-bromo-3,4-difluoro-benzene in 100 ml of THF at 50° C. After the halide has all been added, the mixture is stirred for another hour. The Grignard reagent thus obtained is added dropwise to 18.81 g (0.088 mol) of ethyl 3,4-difluorophenylglyoxylate in 80 ml of THF at 10°-15° C. and the mixture obtained is stirred for 2 hours at 5° C.

Workup

customthe mixture obtained

Sources & evidence

ORD record: ord-4025aced4c7048988b31e777f470e500
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06706726B2

Reaction notes

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