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

HRID 1674156Notes

Reaction equation

HRID 1674156 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-dc2356b681f2448abe1ec47d43d2b096
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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