2-Bromoanisole → 3-bromo-4-methoxybenzenesulfonyl chloride

HRID 1622086Notes

Reaction equation

HRID 1622086 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].[Cl:10][S:11](O)(=[O:13])=[O:12]>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([S:11]([Cl:10])(=[O:13])=[O:12])[CH:5]=[CH:4][C:3]=1[O:8][CH3:9]

Participants

4

Reactant 2

HCID 113582-BromoanisoleHCID 24638Chlorosulfonic acid

Product 1

HCID 38637473-bromo-4-methoxybenzenesulfonyl chlorideYield 98.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1-Bromo-2-methoxy-benzene (1.87 g, 10.0 mmol) was dissolved in chloroform (5 mL) and the solution was cooled in an ice-salt bath to −5° C. to 0° C. The cooled solution was carefully charged with chlorosulfonic acid (2.0 mL, 30.0 mmol) over 30 minutes and the mixture was allowed to warm to room temperature over 1 hour. The mixture then was poured onto chopped ice and transferred to a separatory funnel. The aqueous layer was separated and extracted (×2). The combined organic layers were dried and concentrated to give 3-bromo-4-methoxyphenylsulfonyl chloride (2.80 g, 98%).

Workup

  1. temperaturethe solution was cooled in an ice-salt bath to −5° C. to 0° C
  2. additionThe mixture then was poured
  3. customtransferred to a separatory funnel
  4. customThe aqueous layer was separated
  5. extractionextracted (×2)
  6. customThe combined organic layers were dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-25becbe87eab498e944dbe1fe6dc2382
Source dataset
uspto-grants-2014_07
Patent number
US08778625B2

Reaction notes

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