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

HRID 1508450Notes

Reaction equation

[F:1]C1C=CC=CC=1CC(=O)C(OCC)=O.Br[C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20]Br.[Mg].[C:26]([O:33]CC)(=O)[C:27]([O:29][CH2:30][CH3:31])=[O:28]>>[F:1][C:17]1[CH:18]=[C:19]([CH2:20][C:26](=[O:33])[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:22]=[CH:23][CH:24]=1

Participants

Reactant 4

HCID 7268Diethyl Oxalate

HCID 699793-Bromobenzyl 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-bromobenzyl bromide (1.250 g, 5.00 mmol), magnesium (0.134 g, 5.50 mmol) and diethyl oxalate (1.462 g, 10.00 mmol). The product was isolated in the form of colorless oil in 80% yield and use instantly in next step.

Workup

customThe product was isolated in the form of colorless oil in 80% yield and use instantly in next step

Sources & evidence

ORD record: ord-713c2869a255400e96ee55c004582c15
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221860B2

Reaction notes

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