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

HRID 1357279Notes

Reaction equation

HRID 1357279 reaction equation
[C:1]([Cl:6])(=[O:5])[C:2](Cl)=[O:3].[CH2:7]([C:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2OC=1C(O)=O)[CH2:8][CH2:9][CH3:10].CN(C=O)C>C(Cl)Cl>[CH2:7]([C:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[O:3][C:2]=1[C:1]([Cl:6])=[O:5])[CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 185053403-Butyl-benzofuran-2-carboxylic acid

Product 1

HCID 185053603-Butyl-benzofuran-2-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl Chloride (3.86 mL, 44.2 mmol) was added under nitrogen at room temperature to a solution of 3-butyl-benzofuran-2-carboxylic acid (1.93 g, 8.84 mmol) in 60 mL of methylene chloride. After the addition a catalytic amount of DMF (10 μL) was added and the reaction was stirred at room temperature for 2 h. The solvent was removed under reduced pressure. To remove the excess oxalyl chloride the residue was dissolved in benzene and the solvent removed under reduced pressure to give 3-butyl-benzofuran-2-carbonyl chloride, which was immediately used in step 2 without additional purification.

Workup

  1. additionwas added
  2. customThe solvent was removed under reduced pressure
  3. customTo remove the excess oxalyl chloride the residue
  4. dissolutionwas dissolved in benzene
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-4620a0c77b894392b254633f88f49861
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

Loading…