Dichloromethane → 2,5-Dichloro-4-methylthiophene-3-sulfonyl chloride

반응식

[CH3:1][C:2]1[CH:6]=[CH:5][S:4]C=1.[S:7]([Cl:11])(Cl)(=[O:9])=[O:8].[Cl:12]S(O)(=O)=O.Cl[CH2:18][Cl:19]>>[Cl:12][C:5]1[S:4][C:18]([Cl:19])=[C:2]([CH3:1])[C:6]=1[S:7]([Cl:11])(=[O:9])=[O:8]

참가 물질

반응물 4

HCID 6344Dichloromethane2회

HCID 120243-Methylthiophene

HCID 24638Chlorosulfonic acid

HCID 24648Sulfuryl chloride

생성물 1

HCID 219837962,5-Dichloro-4-methylthiophene-3-sulfonyl chloride수율 25%

반응 조건

온도: 10 °C

실험 절차

To a cooled (10° C.) solution of 3-methylthiophene (5 g, 50 mmol) in dichloromethane (15 mL) was added a solution of sulfuryl chloride (8.6 mL) in dichloromethane (5 mL). The reaction mixture was maintained at 10° C. for 30 minutes, then at ambient temperature for 16 hours. The reaction was concentrated and redissolved in dichloromethane (30 mL) and cooled to −10° C. To the cooled solution was added chlorosulfonic acid (2 mL, 100 mmol). The reaction was maintained at −10° C. for 30 minutes, then at ambient temperature for 16 hours, at which time it was poured into ice water (50 mL) and extracted with dichloromethane (50 mL). The organic layer was dried (Mg2SO4) and concentrated to furnish a brown oil (3.3 g, 25%).