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

HRID 873622Notes

Reaction equation

HRID 873622 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-17192fe5597e47cb962e355daa949261
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

Loading…