Chlorosulfonic acid → 5-fluoro-4-hydroxy-2-methylbenzenesulfonyl Chloride

HRID 216303Notes

Reaction equation

HRID 216303 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[F:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:8]=1[OH:14]>ClCCl>[F:6][C:7]1[C:8]([OH:14])=[CH:9][C:10]([CH3:13])=[C:11]([S:2]([Cl:1])(=[O:5])=[O:3])[CH:12]=1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 182387Phenol, 2-fluoro-5-methyl-

Product 1

HCID 847898185-fluoro-4-hydroxy-2-methylbenzenesulfonyl ChlorideYield 7.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of chlorosulfonic acid (1.5 g, 13.3 mmol) dissolved in 10 mL of dichloromethane was added 2-fluoro-5-methylphenol (1.1 g, 8.86 mmol) dropwise. After 10 minutes, the reaction was quenched by adding to ice water. The reaction was extracted with dichloromethane, washed with brine, dried over MgSO4, filtered, and concentrated to give 150 mg (7.5%) of the title compound.

Workup

  1. customthe reaction was quenched
  2. additionby adding to ice water
  3. extractionThe reaction was extracted with dichloromethane
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2f5080c790b047c2ad93840e8b4185fd
Source dataset
uspto-grants-2012_06
Patent number
US08193227B2

Reaction notes

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