Thionyl Chloride → HCID 15075752, compound

HRID 1916966Notes

Reaction equation

HRID 1916966 reaction equation
[F: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.C1COCC1>[Cl:21][C:6]1([C:5]2[CH:17]=[CH:18][C:2]([F: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

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 820992-(4-Fluorobenzoyl)benzoic acid

Product 1

HCID 15075752HCID 15075752, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

THF (25 mL) was added to 2-(4-fluorobenzoyl)benzoic acid (5 g, 20.4 mmol) followed by thionyl chloride (2.97 mL, 40.9 mmol) and a catalytic amount of DMF (3 drops). The system was stirred under nitrogen for 4 h at room temperature. Removal of the solvent gave 3-chloro-3-(4-fluorophenyl)-3H-isobenzofuran-1-one as a colourless oil (5.35 g, 20.4 mmol, 100%).

Workup

  1. customRemoval of the solvent

Sources & evidence

ORD record
ord-60f9ed02c1de49b384ea22dc02bd0415
Source dataset
uspto-grants-2013_12
Patent number
US08618158B2

Reaction notes

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