Chlorosulfonic acid → 3,5-Dimethyl-1-benzothiophene-2-sulfonyl chloride

HRID 589669Notes

Reaction equation

HRID 589669 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[C:8]([CH3:11])[CH:9]=[CH:10][C:5]=2[S:4][CH:3]=1.[Cl:12][S:13](O)(=[O:15])=[O:14].C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[CH3:1][C:2]1[C:6]2[CH:7]=[C:8]([CH3:11])[CH:9]=[CH:10][C:5]=2[S:4][C:3]=1[S:13]([Cl:12])(=[O:15])=[O:14]

Participants

5

Reactant 3

HCID 24638Chlorosulfonic acidHCID 516892Sodium BicarbonateHCID 2779875Benzo[b]thiophene, 3,5-dimethyl-2×

Product 1

HCID 220414653,5-Dimethyl-1-benzothiophene-2-sulfonyl chlorideYield 40%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3,5-dimethylbenzothiophene (Intermediate 12) (5.0 g, 33.8 mmol) in CHCl3 (70 mL), chlorosulfonic acid (5.6 mL, 85 mmol) was added dropwise at −5° C. The reaction mixture was stirred at 0° C. for 3 h before it was poured into a mixture of ice and NaHCO3 and stirred vigorously for 5 min. The organic phase was immediately separated, dried with MgSO4 and concentrated yielding 3.5 g (40%) of the title compound.

Workup

  1. stirringstirred vigorously for 5 min
  2. customThe organic phase was immediately separated
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cefb835a10fc403aba4a957e68633d4f
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

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