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

HRID 1858002Notes

Reaction equation

HRID 1858002 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-3d2ab25218d44469b3b30b604329f0b8
Source dataset
uspto-grants-2000_11
Patent number
US06150397

Reaction notes

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