반응 #1269817

반응 방정식

benzo[b]thiophene-2-sulfonyl chloride

nitric acid

→

product

Mono nitro-benzo[b]thiophene-2-sulfonyl chloride

용매

dichloromethane

반응 조건

후처리

1. 1
   온도the resulting mixture was refluxed overnight
2. 2
   기타The organic layer was separated
3. 3
   추출the aqueous layer was extracted by 220 mL 2 dichloromethane
4. 4
   건조dried over MgSO4
5. 5
   기타Solvent was then removed by rotary evaporator
6. 6
   기타The crude product was purified by flash column chromatography with an eluent of hexane

실험 절차

To a solution of benzo[b]thiophene-2-sulfonyl chloride (1.165 g, 5 mmol) in 25 mL of dichloromethane was added 3.6 mL of concentrated nitric acid (≧22.05 mol/L) dropwise, the resulting mixture was refluxed overnight and cooled to room temperature before it was poured into 20 gram of crushed ice. The organic layer was separated and the aqueous layer was extracted by 220 mL 2 dichloromethane. The organic layers were combined and dried over MgSO4. Solvent was then removed by rotary evaporator. The crude product was purified by flash column chromatography with an eluent of hexane, followed by a gradient eluent of hexane/ethyl acetate (6/1-3/1) to afford 0.58 g of product (mixture of 65% of 4-nitro-benzo[b]thiophene-2-sulfonyl chloride and 35% of 7-nitro-benzo[b]thiophene-2-sulfonyl chloride).

출처