Sulfuryl chloride → 2-Methyl-1-benzothiophene-3-sulfonyl chloride

Temperature

0 °C

Sulfuryl chloride (9.5 mmoles, 0.76 ml) was added to a stirred solution of dimethylformamide (DMF; 11.2 mmoles, 0.87 ml) at 0° C., and the resulting faint yellow solution was stirred for 20 min at 0° C. 2-Methylbenzo[b]thiophene (5.6 mmoles, 0.83 g) was then added, the reaction mixture was diluted with 2 ml of DMF, and then heated to 85° C. After 2.5 hrs at 85° C., the brown reaction mixture was cooled to ambient temperature and added to ice (≈100 ml). The aqueous phase was extracted with ethyl acetate (100 ml), and the organic phase was dried (MgSO4), filtered and concentrated to collect an orange-brown solid. Flash chromatography (4% ethyl acetate/hexanes) provided 0.89 g (64%) of 2-methylbenzo[b]thiophene-3-sulfonyl chloride as a yellow solid.

1. temperatureheated to 85° C
2. waitAfter 2.5 hrs at 85° C.
3. temperaturethe brown reaction mixture was cooled to ambient temperature
4. extractionThe aqueous phase was extracted with ethyl acetate (100 ml)
5. dry with materialthe organic phase was dried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated
8. customto collect an orange-brown solid

ORD record

ord-9d4c1b35862a43bbbd70612387331036

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06613804B2