Hydrochloric Acid → 5-(4-Fluoro-phenylsulfonyl)-6-methoxy-2-methylsulfonylnaphthalene

HRID 1738304Notes

Reaction equation

HRID 1738304 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][O:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:13]=2)[CH:8]=1.[F:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.Cl>ClCCCl>[F:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([C:8]2[C:7]([O:6][CH3:5])=[CH:16][CH:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][C:12]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13]3)(=[O:30])=[O:29])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 95884-Fluorobenzenesulfonyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 154346222-Methoxy-6-methylsulfonylnaphthalene

Product 1

HCID 154346175-(4-Fluoro-phenylsulfonyl)-6-methoxy-2-methylsulfonylnaphthaleneYield 16%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Aluminum chloride (1.13 g, 8.46 mmol) was added to a solution of 2-methoxy-6-methylsulfonylnaphthalene (1.0 g, 4.2 mmol) [prepared as described in example 2 above], and 4-fluorobenzenesulfonyl chloride (1.65 g, 8.46 mmol) in 1,2 dichloroethane (40 ml). The reaction mixture was heated at reflux for 16 h, and then poured into 2N HCl and extracted into methylene chloride. The organic layer was separated, washed with water and brine, and dried over sodium sulfate. Purification by flash chromatography gave 0.1 g of 5-(4-fluoro-phenylsulfonyl)-6-methoxy-2-methylsulfonylnaphthalene as a solid (16% yield).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 16 h
  3. extractionextracted into methylene chloride
  4. customThe organic layer was separated
  5. washwashed with water and brine
  6. dry with materialdried over sodium sulfate
  7. customPurification by flash chromatography

Sources & evidence

ORD record
ord-95a0864653124a8cbab2ecb4d5477662
Source dataset
uspto-grants-1999_10
Patent number
US05962531

Reaction notes

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