Dimethylformamide → 2-Butyl-benzofuran-3-carbonyl chloride

HRID 493476Notes

Reaction equation

HRID 493476 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[CH2:7]([C:11]1[O:12][C:13]2[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=2C=1C(O)=O)[CH2:8][CH2:9][CH3:10].CN(C=O)C>C(Cl)Cl.C1C=CC=CC=1>[CH2:7]([C:11]1[O:12][C:13]2[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=2[C:1]=1[C:2]([Cl:4])=[O:3])[CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 185052842-Butyl-benzofuran-3-carboxylic acid

Product 1

HCID 185053462-Butyl-benzofuran-3-carbonyl chloride

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6344DichloromethaneSolvent

Procedure

Oxalyl Chloride (460 μL, 5.27 mmol) was added under nitrogen at room temperature to a solution of 2-butyl-benzofuran-3-carboxylic acid (230 mg, 1.05 mmol), prepared in the previous step, in 10 mL of methylene chloride. After the addition a catalytic amount of DMF was added and the reaction stirred at room temperature for 1.5 h. The solvent was removed under reduced pressure to give a brown oil. The oil was dissolved in benzene and the solvent removed under reduced pressure to give 2-butyl-benzofuran-3-carbonyl chloride as a brown oil. The material was immediately used in the following reaction with out additional purification.

Workup

  1. additionwas added
  2. customThe solvent was removed under reduced pressure
  3. customto give a brown oil
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-042285b861754c4d87f5d248fbb90ee2
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

Loading…