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

HRID 2355111Notes

Reaction equation

HRID 2355111 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>[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

5

Reactant 3

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

Product 1

HCID 185053462-Butyl-benzofuran-3-carbonyl chlorideYield 92.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (6 mL, 68.8 mmol) was added under nitrogen at room temperature to a solution of 2-butyl-benzofuran-3-carboxylic acid (3.00 g, 13.7 mmol), prepared in the previous step, in 40 mL of methylene chloride. After the addition 10 μL of DMF was added and the reaction stirred at room temperature for 3 h. The solvent and the excess oxalyl chloride were removed under reduced pressure. To remove any residual oxalyl chloride the residue was taken up in benzene and then concentrated under reduced pressure to give 2-butyl-benzofuran-3-carbonyl chloride (3.00 g, 92%) as a white solid that was used in the next step without additional purification.

Workup

  1. additionwas added
  2. customThe solvent and the excess oxalyl chloride were removed under reduced pressure
  3. customTo remove any residual oxalyl chloride the residue
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bceb95a6e32740ad8213cfe966f42198
Source dataset
uspto-grants-2010_07
Patent number
US07754747B2

Reaction notes

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