1-(Bromomethyl)-2,3-difluoro-benzene → Ethyl 2-(2,3-difluorobenzyl)-3-oxobutyrate

HRID 1718826Notes

Reaction equation

HRID 1718826 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:4]=1[F:10].[Na].[C:12]([O:18][CH2:19][CH3:20])(=[O:17])[CH2:13][C:14]([CH3:16])=[O:15]>O1CCCC1>[F:10][C:4]1[C:5]([F:9])=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][CH:13]([C:14](=[O:15])[CH3:16])[C:12]([O:18][CH2:19][CH3:20])=[O:17]

Participants

4

Reactant 2

HCID 5179841-(Bromomethyl)-2,3-difluoro-benzeneHCID 87089461Ethyl acetoacetatesodium salt

Product 1

HCID 57460769Ethyl 2-(2,3-difluorobenzyl)-3-oxobutyrateYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(bromomethyl)-2,3-difluorobenzene (1.6 g) and ethyl acetoacetate sodium salt (2.36 g) in tetrahydrofuran (20 mL) was stirred for 12 hr. The insoluble material was filtered off, and the filtrate was concentrated. The residue was purified by silica gel column chromatography to give the title compound (1.56 g, 79%) as a colorless viscous oil.

Workup

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7aac95f8b16644ff9420b1eaeb712a43
Source dataset
uspto-grants-2010_09
Patent number
US07803940B2

Reaction notes

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