Chloroform → 2-(2-Bromoacetyl)benzofuran-5-carbonitrile

HRID 1901341Notes

Reaction equation

HRID 1901341 reaction equation
[C:1]([C:4]1[O:5][C:6]2[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][C:7]=2[CH:8]=1)(=[O:3])[CH3:2].[Br:15]Br.C(Cl)(Cl)Cl>ClCCl>[Br:15][CH2:2][C:1]([C:4]1[O:5][C:6]2[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][C:7]=2[CH:8]=1)=[O:3]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 24408BromineHCID 128136342-Acetyl-5-benzofurancarbonitrile

Product 1

HCID 102647592-(2-Bromoacetyl)benzofuran-5-carbonitrileYield 70.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

21.0 g of 2-acetyl-5-benzofurancarbonitrile was dissolved in 300 ml of dichloromethane. With stirring at a temperature of -10° C., 30 ml of dichloromethane solution containing 18.2 g of bromine was added dropwise to the above solution. After gradually warming up to ice-cold temperature, the resulting reaction solution was mixed with chloroform and washed with 10% sodium thiosulfate aqueous solution. After drying the organic layer and subsequent concentration to dryness, the resulting residue was recrystallized from a benzene/n-hexane mixture to obtain 21.0 g of 2-(2-bromo-1-oxoethyl)-5-benzofurancarbonitrile in the form of colorless crystals.

Workup

  1. additionwas added dropwise to the above solution
  2. temperatureAfter gradually warming up to ice-cold temperature
  3. customthe resulting reaction solution
  4. washwashed with 10% sodium thiosulfate aqueous solution
  5. customAfter drying
  6. concentrationthe organic layer and subsequent concentration to dryness
  7. customthe resulting residue was recrystallized from a benzene/n-hexane mixture

Sources & evidence

ORD record
ord-dc8620680ebd4d46806740f725a56eb1
Source dataset
uspto-grants-1996_11
Patent number
US05576343

Reaction notes

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