Diethyl Oxalate → Ethyl 3-(3-fluorophenyl)-2-oxopropanoate

HRID 1508421Notes

Reaction equation

F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9](=[O:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11].[F:16]C1C=C(C=CC=1)CBr.[Mg].C(OCC)(=O)C(OCC)=O>>[F:16][C:7]1[CH:2]=[C:3]([CH2:8][C:9](=[O:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:4]=[CH:5][CH:6]=1

Participants

Reactant 4

HCID 7268Diethyl Oxalate

HCID 680073-Fluorobenzyl bromide

HCID 5462224Magnesium

HCID 18370709Ethyl (2-fluorophenyl)pyruvate

Product 1

HCID 18370708Ethyl 3-(3-fluorophenyl)-2-oxopropanoateYield 80%

Procedure

The title compound was prepared as described for B4 using 3-fluorobenzyl bromide (1.250 g, 8.64 mmol), magnesium (0.231 g, 9.51 mmol) and diethyl oxalate (2.52 g, 17.30 mmol) in the form of colorless oil in 80% yield and used instantly in next step.

Sources & evidence

ORD record: ord-1adcaae4a531460897715aecfe67c960
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221860B2

Reaction notes

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