Sulfuryl chloride → 4-Methoxy-2,3-dimethylbenzenesulfonyl chloride

HRID 1174522

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

2,3-Dimethylanisole (1 cm3, 7.23 mmol) was dissolved into dichloromethane (4 cm3) and cooled to 0° C. Chlorosulfonyl chloride (2 cm3, 30.0 mmol) was then added dropwise, over 10 min and once the addition was completed the mixture was allowed to warm to room temperature and stirred for a further 45 min. The reaction was then quenched by the slow addition of ice/water (50 cm3, CARE, exotherm) before further dichloromethane (30 cm3) and water (30 cm3) were added and the organic layer was collected. The aqueous layer was washed with dichloromethane (15 cm3) and then organic extracts were combined and washed with saturated aqueous sodium chloride solution (70 cm3) before being dried over sodium sulfate. The solvent was evaporated under reduced pressure to afford title compound (1.6 g, 6.82 mmol, 94% yield).

Workup

additiononce the addition
temperatureto warm to room temperature
customThe reaction was then quenched by the slow addition of ice/water (50 cm3, CARE, exotherm) before further dichloromethane (30 cm3) and water (30 cm3)
additionwere added
customthe organic layer was collected
washThe aqueous layer was washed with dichloromethane (15 cm3)
washwashed with saturated aqueous sodium chloride solution (70 cm3)
dry with materialbefore being dried over sodium sulfate
customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-1a5e44fa474642838b6f1af30a12104c
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07838518B2

Linked notes

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