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

HRID 1515417Notes

Reaction equation

HRID 1515417 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): δ 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-8d594c1306e543a598b22d8d456cb638
Source dataset
uspto-grants-2012_07
Patent number
US08222424B2

Reaction notes

Loading…