Anisole → 2-Fluoro-5-(4-methoxy-benzoyl)-benzenesulfonyl chloride

HRID 1810150Notes

Reaction equation

HRID 1810150 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][S:6]([C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[F:18])[C:12](Cl)=[O:13])(=[O:8])=[O:7].[C:19]1([O:25][CH3:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)Cl>[F:18][C:17]1[CH:16]=[CH:15][C:11]([C:12](=[O:13])[C:22]2[CH:23]=[CH:24][C:19]([O:25][CH3:26])=[CH:20][CH:21]=2)=[CH:10][C:9]=1[S:6]([Cl:5])(=[O:8])=[O:7]

Participants

5

Reactant 3

HCID 7519AnisoleHCID 6451240Aluminum(III) ChlorideHCID 581074393-(Chlorosulfonyl)-4-fluorobenzoyl chloride

Product 1

HCID 581074472-Fluoro-5-(4-methoxy-benzoyl)-benzenesulfonyl chlorideYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of aluminium chloride (2.1 g, 15.7 mmol) in methylene chloride (50 mL) is added 3-chlorosulfonyl-4-fluoro benzoyl chloride (10.5 mmol). The reaction mixture is stirred at room temperature for 10 minutes then anisole (1.36 g, 12.5 mmol) is added. After the mixture is stirred at room temperature for 16 h, the reaction is quenched with 6 N HCl, and extracted with methylene chloride three times. The combined organic layers are washed with a saturated sodium chloride solution, dried with magnesium sulfate, and concentrated in vacuo. Purification by silica gel chromatography (ethyl acetate/hexane: 1:9) followed by recrystallization (methylene chloride-hexane) provides 1.8 g (54% yield) of the title compound as a white solid. 1H NMR (CDCl3): δ 8.41 (m, 1H), 8.20 (m, 1H), 7.82 (d, J=15 Hz, 2H), 7.50 (t, 1H), 7.08 (d, J=15 Hz, 2H), 3.95 (s, 3H).

Workup

  1. stirringAfter the mixture is stirred at room temperature for 16 h
  2. customthe reaction is quenched with 6 N HCl
  3. extractionextracted with methylene chloride three times
  4. washThe combined organic layers are washed with a saturated sodium chloride solution
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification by silica gel chromatography (ethyl acetate/hexane: 1:9)
  8. customfollowed by recrystallization (methylene chloride-hexane)

Sources & evidence

ORD record
ord-5363a8d6015b4c88acc9b9507d2f0bf5
Source dataset
uspto-grants-2013_01
Patent number
US08362063B2

Reaction notes

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