Chlorosulfonic acid → 2-Bromo-4,5-dimethoxybenzene-1-sulfonyl chloride

HRID 1795194Notes

Reaction equation

HRID 1795194 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:10][CH3:11])[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.[Cl:12][S:13](O)(=[O:15])=[O:14]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([O:10][CH3:11])[C:5]([O:8][CH3:9])=[CH:6][C:7]=1[S:13]([Cl:12])(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 76114Benzene, 4-bromo-1,2-dimethoxy-

Product 1

HCID 49624752-Bromo-4,5-dimethoxybenzene-1-sulfonyl chlorideYield 79.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of 4-bromoveratrole (15 mL, 100 mmol) in dichloromethane (100 mL) was added dropwise chlorosufonic acid (26 mL, 400 mmol). The reaction was allowed to slowly warm to ambient temperature and maintained for 3 hours, at which time it was concentrated and diluted with ether (300 mL). The resultant solution was then washed with ice cold water (2×250 mL) and brine (100 mL), dried over magnesium sulfate, and concentrated to furnish a grayish powder (25 g, 78%).

Workup

  1. temperaturemaintained for 3 hours, at which time it
  2. concentrationwas concentrated
  3. additiondiluted with ether (300 mL)
  4. washThe resultant solution was then washed with ice cold water (2×250 mL) and brine (100 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-46af6e94c9c24c6281c66808f94be677
Source dataset
uspto-grants-2006_04
Patent number
US07026349B2

Reaction notes

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