Dimethylformamide → 2-Benzofurancarbonyl chloride

HRID 1357214Notes

Reaction equation

HRID 1357214 reaction equation
CN(C=O)C.[O:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH:8]=[C:7]1[C:15]([OH:17])=O.C(Cl)(=O)C([Cl:21])=O>C(Cl)Cl>[O:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH:8]=[C:7]1[C:15]([Cl:21])=[O:17]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 10331Benzofuran-2-carboxylic acidHCID 65578Oxalyl chloride

Product 1

HCID 389492-Benzofurancarbonyl chlorideYield 102.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DMF (75 μL) was added under nitrogen to a solution of benzofuran-2-carboxylic acid (5.0 g, 30.8 mmol) and oxalyl chloride (13.3 mL, 154 mmol) in 175 mL of methylene chloride at room temperature. After the addition the reaction was stirred at room temperature for 1 h. The solvent and excess oxalyl chloride were removed under reduced pressure to give 5.72 g of a white solid which was used in the next step without additional purification.

Workup

  1. additionAfter the addition the reaction
  2. customThe solvent and excess oxalyl chloride were removed under reduced pressure

Sources & evidence

ORD record
ord-51d087960ce243a2b73131f7a20f6bc9
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

Loading…