4-Fluorobenzoyl chloride → HCID 15434620, compound

HRID 1858000Notes

Reaction equation

HRID 1858000 reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:9]=2)[CH:4]=1.[F:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl.Cl>[F:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([C:4]2[C:3]([OH:2])=[CH:12][CH:11]=[C:10]3[C:5]=2[CH:6]=[CH:7][C:8]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9]3)=[O:23])=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 678794-Fluorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 154346222-Methoxy-6-methylsulfonylnaphthalene

Product 1

HCID 15434620HCID 15434620, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 313Hydrochloric AcidSolvent

Procedure

To a solution of 2-methoxy-6-methylsulfonylnaphthalene (0.93 g, 3.93 mmol), [prepared as described in step 2 above], in 1,2-dichloroethane (40 ml) was added 4-fluorobenzoyl chloride (0.93 ml, 7.87 mmol) and aluminum chloride (1.05 g, 7.87 mmol) and the reaction mixture was heated at reflux. After 16 h, the reaction mixture was poured in 2N HCl and extracted into methylene chloride. The organic layer was separated and washed with water and dried over sodium sulfate. The solvent was removed in vacuo and the crude product was purified by flash chromatography (gradient elution 10-60% ethyl acetate/hexanes) to give 1.2 g of 5-(4-fluorobenzoyl)-6-hydroxy-2-methylsulfonyl-naphthalene as a tan solid (89% yield).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux
  3. extractionextracted into methylene chloride
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was removed in vacuo
  8. customthe crude product was purified by flash chromatography (gradient elution 10-60% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-aad0edccd51a44dfb8fde8d03bd5882e
Source dataset
uspto-grants-2000_11
Patent number
US06150397

Reaction notes

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