Chlorosulfonic acid → 5-bromo-3-methyl-1-benzothiophene-2-sulfonyl chloride

HRID 589664Notes

Reaction equation

HRID 589664 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[Br:6][C:7]1[CH:8]=[CH:9][C:10]2[S:14][CH:13]=[C:12]([CH3:15])[C:11]=2[CH:16]=1>C(Cl)(Cl)Cl>[Br:6][C:7]1[CH:8]=[CH:9][C:10]2[S:14][C:13]([S:2]([Cl:1])(=[O:5])=[O:3])=[C:12]([CH3:15])[C:11]=2[CH:16]=1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 141757645-Bromo-3-methyl-1-benzothiophene2×

Product 1

HCID 27355915-bromo-3-methyl-1-benzothiophene-2-sulfonyl chlorideYield 15,820.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

Chlorosulfonic acid (2.20 ml, 0.033 mmol) was added dropwise at −5° C. to a solution of 5-bromo-3-methylbenzothiophene (Intermediate 9) (3.0 g, 13.2 mmol) in CHCl3 (30 mL). The reaction mixture was stirred at 0° C. for 3 h, and then poured into a mixture of ice/NaHCO3 and stirred vigorously for 5 min. The organic phase was immediately separated, dried and concentrated to give the title compound (1.70 g, 39%).

Workup

  1. stirringstirred vigorously for 5 min
  2. customThe organic phase was immediately separated
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-39d18a88475e4d4299d79ad7130e426a
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

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