2-Chloroanisole → 3-Chloro-4-methoxybenzene-1-sulfonyl chloride

HRID 2181847Notes

Reaction equation

HRID 2181847 reaction equation
[Cl: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>[Cl: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 130112-ChloroanisoleHCID 24638Chlorosulfonic acid

Product 1

HCID 167674273-Chloro-4-methoxybenzene-1-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A stirred solution of 2-chloroanisole (8.90 mL, 70.1 mmol) in chloroform (100 mL) was cooled to 0° C., and treated drop-wise with chlorosulfonic acid (9.3 mL, 140 mmol). After stirring at room temperature for 14 hours, the reaction mixture was poured into ice-water (250 mL) and the separated, aqueous phase extracted with chloroform (2×50 mL). The combined organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to a viscous oil which crystallized upon standing (8.58 g, 52%), m.p. 78° C.;

Workup

  1. extractionthe separated, aqueous phase extracted with chloroform (2×50 mL)
  2. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo to a viscous oil which
  5. customcrystallized

Sources & evidence

ORD record
ord-231ffddf0f0348339d6f871f38d30a9d
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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