Chlorosulfonic acid → 4-(2-Methylpropoxy)benzene-1-sulfonyl chloride

Temperature

-45 °C

To a stirring solution of isobutoxybenzene (0.60 g, 4.0 mmol) in dichloromethane (5 mL) at −45° C. was added chlorosulfonic acid (0.6 mL, 9.1 mmol) dropwise, and the reaction mixture was stirred at −45° C. for 1 h. The reaction mixture was then warmed to 0° C. and additional chlorosulfonic acid (0.6 mL, 9.1 mmol) was added dropwise. The reaction mixture was then stirred at 0° C. for 1 h and poured into ice. The aqueous layer was extracted with ethyl acetate and the organic layer was dried (Na2SO4), filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography (SiO2, 5-10% ethyl acetate in hexanes) to give 4-isobutoxybenzene-1-sulfonyl chloride (0.32 g, 1.1 mmol, 28%).

1. temperatureThe reaction mixture was then warmed to 0° C.
2. stirringThe reaction mixture was then stirred at 0° C. for 1 h
3. additionpoured into ice
4. extractionThe aqueous layer was extracted with ethyl acetate
5. dry with materialthe organic layer was dried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe crude residue was purified by flash chromatography (SiO2, 5-10% ethyl acetate in hexanes)

ORD record

ord-4140584514834af1a21b7d886144ff60

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916601B2