Fluorobenzene → 1-(4-Fluorophenyl)-2-(4-methylsulfonylphenyl)ethanone

HRID 1090866Notes

Reaction equation

HRID 1090866 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16](Cl)=[O:17])=[CH:11][CH:10]=1)(=[O:8])=[O:7].[F:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:16](=[O:17])[CH2:15][C:12]2[CH:13]=[CH:14][C:9]([S:6]([CH3:5])(=[O:8])=[O:7])=[CH:10][CH:11]=2)=[CH:22][CH:21]=1

Participants

4

Reactant 3

HCID 10008Fluorobenzene2×HCID 6451240Aluminum(III) ChlorideHCID 15020185HCID 15020185, compound

Product 1

HCID 112433011-(4-Fluorophenyl)-2-(4-methylsulfonylphenyl)ethanoneYield 51%

Conditions

Temperature
20 °C

Procedure

Thereafter 102 g (0.765 mole) of anhydrous aluminum chloride was suspended in 200 ml of fluorobenzene. To the suspension was added dropwise a suspension of 120 g of the 4-methylsulfonylphenylacetyl chloride obtained above in 200 ml of fluorobenzene at a temperature of 0° to 3° C. The reaction vessel used was rinsed with 30 ml of fluorobenzene and the mixture was stirred at 20° C. for 4 hours. The reaction mixture was gradually poured into a mixture of ice water and hydrochloric acid and left to stand overnight, giving gummy solids. The solids were collected by filtration. The organic layer was separated from the filtrate and subjected to distillation under reduced pressure to recover 200 ml (52%) of fluorobenzene. The gummy solids were dissolved in dichloromethane, washed sequentially with water, a 5% aqueous solution of sodium bicarbonate and a saturated saline solution and dried over magnesium sulfate. The dichloromethane was distilled off and the resulting crystals were washed with diethyl ether, giving 77 g (51%) of 1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)ethanone as pale yellow solids.

Workup

  1. additionTo the suspension was added dropwise
  2. washThe reaction vessel used was rinsed with 30 ml of fluorobenzene
  3. additionThe reaction mixture was gradually poured into a mixture of ice water and hydrochloric acid
  4. waitleft
  5. waitto stand overnight
  6. customgiving gummy solids
  7. filtrationThe solids were collected by filtration
  8. customThe organic layer was separated from the filtrate
  9. distillationsubjected to distillation under reduced pressure
  10. customto recover 200 ml (52%) of fluorobenzene
  11. dissolutionThe gummy solids were dissolved in dichloromethane
  12. washwashed sequentially with water
  13. dry with materiala 5% aqueous solution of sodium bicarbonate and a saturated saline solution and dried over magnesium sulfate
  14. distillationThe dichloromethane was distilled off
  15. washthe resulting crystals were washed with diethyl ether

Sources & evidence

ORD record
ord-4f767e392ba64e36aeacefc5f49def6d
Source dataset
uspto-grants-1992_01
Patent number
US05082974

Reaction notes

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