Sodium hydride → HCID 117690248, compound

HRID 508116Notes

Reaction equation

[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4]P(=O)(OCC)OCC.[H-].[Na+].[F:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[C:27](=O)[CH3:28]>CN(C=O)C.O>[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH:4]=[C:27]([C:21]1[CH:22]=[CH:23][C:24]([F:26])=[CH:25][C:20]=1[F:19])[CH3:28]

Participants

Conditions

Temperature: 3 °C

Procedure

At 3° C., a solution of diethyl 2-chlorobenzylphosphonate (2.00 g, 7.61 mmol) in dry DMF (30 ml) was added to a stirred suspension of sodium hydride (60% by weight suspension in mineral oil, 365 mg, 9.13 mmol; freshly washed with dry heptane) in dry DMF (20 ml). After 1 h of stirring at 3° C., a solution of 2′,4′-difluoroacetophenone (1.31 g, 8.37 mmol) in dry DMF (20 ml) was added dropwise. The resulting mixture was stirred at RT for 68 h and then diluted with water and extracted with diethyl ether. The organic phase was dried and concentrated to dryness under reduced pressure, and the residue was purified by chromatography on silica gel, which gave 1-[1-(2-chlorophenyl)prop-1-en-2-yl]-2,4-difluorobenzene as a 93/7 mixture of diastereoisomers [colourless solid, 560 mg, yield 26%; GC/MS: m/z=264 (M+); HPLC/MS: log P(HCOOH)=5.05 (major diastereoisomer), 5.34 (minor diastereoisomer)].

Workup

washfreshly washed with dry heptane) in dry DMF (20 ml)
stirringThe resulting mixture was stirred at RT for 68 h
extractionextracted with diethyl ether
customThe organic phase was dried
concentrationconcentrated to dryness under reduced pressure
customthe residue was purified by chromatography on silica gel, which

Sources & evidence

ORD record: ord-90b7e176bc064118b278806c0ba6dfbd
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09095136B2

Reaction notes

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