Chlorosulfonic acid → HCID 59654422, compound

HRID 2242556Notes

Reaction equation

HRID 2242556 reaction equation
[Br:1][C:2]1[C:6]([O:7][CH3:8])=[CH:5][S:4][CH:3]=1.[Cl:9][S:10](O)(=[O:12])=[O:11]>C(Cl)Cl>[Br:1][C:2]1[C:6]([O:7][CH3:8])=[C:5]([S:10]([Cl:9])(=[O:12])=[O:11])[S:4][CH:3]=1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 138062173-Bromo-4-methoxythiophene

Product 1

HCID 59654422HCID 59654422, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 3-bromo-4-methoxythiophene (550 mg, 2.85 mmol), prepared in Step C above, in 30 mL of methylene chloride at −78° C. was added dropwise along the inside wall of the flask chlorosulfonic acid (0.48 mL, 7.21 mmol). The mixture was stirred at −78° C. for 10 min, continued at room temperature for 1 h, and filtered through a 1-in silica gel pad, rinsing with methylene chloride. The filtrate was concentrated in vacuuo to give 270 mg of 4-bromo-3-methoxy-2-thiophene sulfonylchloride (33%) as a light yellow oil.

Workup

  1. waitcontinued at room temperature for 1 h
  2. filtrationfiltered through a 1-in silica gel pad
  3. washrinsing with methylene chloride
  4. concentrationThe filtrate was concentrated in vacuuo

Sources & evidence

ORD record
ord-5a95dc7dcd9b4178abb68603204140a8
Source dataset
uspto-grants-2010_03
Patent number
US07671212B2

Reaction notes

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