Oxalyl chloride → 2,3-Dihydro-1-benzofuran-7-carbonyl chloride

HRID 844573

Reaction equation

HRID 844573 reaction equation
[O:1]1[CH2:5][CH2:4][C:3]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]([OH:12])=O)[C:2]1=2.C(Cl)(=O)C([Cl:16])=O>ClCCl.CN(C)C=O>[O:1]1[CH2:5][CH2:4][C:3]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]([Cl:16])=[O:12])[C:2]1=2

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 27950142,3-Dihydro-1-benzofuran-7-carboxylic acid

Product 1

HCID 27950162,3-Dihydro-1-benzofuran-7-carbonyl chlorideYield 98.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

2,3-Dihydrobenzo[b]furan-7-oic acid (3 g) (see Preparation 32) was suspended in anhydrous dichloromethane (30 ml) and oxalyl chloride (3.5 g) added, followed by addition of dimethylformamide (3 drops). The mixture was stirred at room temperature for 2.5 hours, the solvent then removed under reduced pressure, the resulting residue dissolved in dichloromethane and the solvent removed under reduced pressure. The residue was again dissolved in dichloromethane and the solvent removed under reduced pressure to give 2,3-dihydrobenzo[b]furan-7-oyl chloride as a pink solid (3.3 g).

Workup

  1. customthe solvent then removed under reduced pressure
  2. dissolutionthe resulting residue dissolved in dichloromethane
  3. customthe solvent removed under reduced pressure
  4. dissolutionThe residue was again dissolved in dichloromethane
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-1f85b15f8e274e999f0c849357aa9b83
Source dataset
uspto-grants-2002_04
Patent number
US06380396B1

Linked notes

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