Anisole → 3-(4-Methoxy-benzoyl)-benzenesulfonyl chloride

HRID 873618Notes

Reaction equation

HRID 873618 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][S:6]([C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12](Cl)=[O:13])(=[O:8])=[O:7].[C:18]1([O:24][CH3:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>ClCCl>[CH3:25][O:24][C:18]1[CH:23]=[CH:22][C:21]([C:12]([C:11]2[CH:10]=[C:9]([S:6]([Cl:5])(=[O:8])=[O:7])[CH:17]=[CH:16][CH:15]=2)=[O:13])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7519AnisoleHCID 77671Benzoyl chloride, 3-(chlorosulfonyl)-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 581074213-(4-Methoxy-benzoyl)-benzenesulfonyl chlorideYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere, aluminum chloride (7.5 g, 56.5 mmol) is slurried in dichloromethane (150 mL) then 3-chlorosulfonyl-benzoyl chloride (7.5 g, 31.4 mmol) is added and allowed to stir at ambient temperature for 10 minutes. Anisole (4.06 g, 37.65 mmol) is added. The reaction is allowed to stir at ambient temperature for 18 hours. The reaction mixture is poured over ice-cold 6 N HCl and extracted with dichloromethane to give a purple oil. Purification by silica gel chromatography (10% ethyl acetate in hexanes) yielded 4 g (41% yield) of the title compound as a yellow powder. 1H NMR (CDCl3): 8.5 (t, 1H, J=1.7 Hz), 8.25 (m, 1H), 8.1 (m, 1H), 7.7-7.9 (m, 3H), 7.0 (d, 2H, J=6.9 Hz), 3.9 (s, 3H).

Workup

  1. stirringto stir at ambient temperature for 18 hours
  2. extractionextracted with dichloromethane
  3. customto give a purple oil
  4. customPurification by silica gel chromatography (10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-bbffc03794904f0cb0d6d68958d759c0
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

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