Chlorosulfonic acid → 3-Fluoro-4-methoxybenzene-1-sulfonyl chloride

HRID 2181854Notes

Reaction equation

HRID 2181854 reaction equation
[F: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>[F: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 24638Chlorosulfonic acidHCID 675762-Fluoroanisole

Product 1

HCID 27745403-Fluoro-4-methoxybenzene-1-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A stirred solution of 2-fluoroanisole (33.7 mL, 301 mmol) in chloroform (250 mL) was cooled to 0° C. and treated drop-wise with chlorosulfonic acid (50.0 mL, 752 mmol). After stirring at room temperature for 14 hours, the reaction mixture was poured into ice-water (700 mL) and the separated, aqueous phase extracted with chloroform (2×200 mL). The combined organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to yield 3-fluoro-4-methoxybenzenesulfonyl chloride as a fine, white solid (58.6 g, 87%), m.p. 80° C.;

Workup

  1. extractionthe separated, aqueous phase extracted with chloroform (2×200 mL)
  2. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-faaa60fbed354fbb923df06198a7a9b5
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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