Thionyl Chloride → 5-chloro-7-(chloromethyl)-2,2-dimethylbenzofuran-3(2H)-one

HRID 1909552Notes

Reaction equation

HRID 1909552 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:14]O)[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[C:7](=[O:12])[C:6]=2[CH:13]=1.S(Cl)([Cl:18])=O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:14][Cl:18])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[C:7](=[O:12])[C:6]=2[CH:13]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 585665785-chloro-7-(hydroxymethyl)-2,2-dimethylbenzofuran-3(2H)-one

Product 1

HCID 585667245-chloro-7-(chloromethyl)-2,2-dimethylbenzofuran-3(2H)-one

Procedure

A solution of 5-chloro-7-(hydroxymethyl)-2,2-dimethylbenzofuran-3(2H)-one (656) (278 mg, 1.23 mmol) in neat thionyl chloride (5 mL) was stirred at room temperature for 48 hours. The reaction was concentrated to obtain 5-chloro-7-(chloromethyl)-2,2-dimethylbenzofuran-3(2H)-one (657) as a brown/grey solid.

Workup

  1. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-e1264c8417d249e7a5b92921d32fcd7e
Source dataset
uspto-grants-2013_12
Patent number
US08598374B2

Reaction notes

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