Thionyl Chloride → 3-Chloro-3-(4-chlorophenyl)-2-benzofuran-1(3H)-one

HRID 2381564Notes

Reaction equation

HRID 2381564 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=[O:11])=O)=[CH:4][CH:3]=1.S(Cl)([Cl:21])=O>CN(C=O)C>[Cl:21][C:6]1([C:5]2[CH:17]=[CH:18][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:8]2[C:9](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:10](=[O:12])[O:11]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 665642-(4'-Chlorobenzoyl)benzoic acid

Product 1

HCID 126920383-Chloro-3-(4-chlorophenyl)-2-benzofuran-1(3H)-oneYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

Distilled THF (25 mL) was added to 2-(4-chlorobenzoyl)benzoic acid (1 g, 3.8 mmol) followed by thionyl chloride (0.55 mL, 7.6 mmol) and a catalytic amount of DMF (3 drops). The system was stirred under nitrogen for 4 h at room temperature and monitored by TLC. Removal of the solvent gave 3-chloro-3-(4-chlorophenyl)-3H-isobenzofuran-1-one as a colourless oil (1.06 g, 3.8 mmol, 100%).

Workup

  1. distillationDistilled THF (25 mL)
  2. customRemoval of the solvent

Sources & evidence

ORD record
ord-a79c7be09fab4729b37ccf2a233a9b96
Source dataset
uspto-grants-2012_09
Patent number
US08258175B2

Reaction notes

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