2-Bromothiophene → 5-Bromothiophene-2-sulfonyl chloride

Chlorosulfonic acid was added dropwise over 20 min. to a cold solution (-78° C.) of 2-bromothiophene (16.3 g, 100 mmol) in methylene chloride (50 ml). After addition of chlorosulfonic acid complete, the cold bath was removed. The reaction mixture was allowed to attain room temperature slowly (2 h), was added dropwise onto the crushed ice (1000 g) and was extracted with methylene chloride (4×100 ml). The combined organic layers was dried over MgSO4, filtered and the solvent was removed under reduced pressure to give a crude product. This was purified by column chromatography using hexane as eluent to give 5-bromothiophene-2-sulfonyl chloride (22 g, 75% yield).

1. customthe cold bath was removed
2. customto attain room temperature
3. customslowly (2 h)
4. additionwas added dropwise onto the crushed ice (1000 g)
5. extractionwas extracted with methylene chloride (4×100 ml)
6. dry with materialThe combined organic layers was dried over MgSO4
7. filtrationfiltered
8. customthe solvent was removed under reduced pressure
9. customto give a crude product
10. customThis was purified by column chromatography

ORD record

ord-0c10b76544af46739897ebbf04f320c1

Source dataset

uspto-grants-1997_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05594021