Benzene → (2,4-Dimethyl-phenyl)-(4-fluoro-phenyl)-methanone

HRID 1262721Notes

Reaction equation

HRID 1262721 reaction equation
Cl[C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:9]=2[CH3:15])=[O:7])=[CH:4][CH:3]=1.[F-:18].[Cs+].CN1CCCC1=O.C1C=CC=CC=1>O>[F:18][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:9]=2[CH3:15])=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 13387N-methyl-2-pyrrolidoneHCID 25953Cesium fluorideHCID 6105854-Chloro-2',4'-dimethylbenzophenone

Product 1

HCID 10242880(2,4-Dimethyl-phenyl)-(4-fluoro-phenyl)-methanoneYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 12.2 g (0.05 mols) of 4-chloro-2',4'-dimethylbenzophenone, 12.1 g (0.08 mols) of cesium fluoride and 20 g of N-methylpyrrolidone were 5 ml of benzene added and water in the reaction system was removed together with benzene by azeotropy. The reaction was carried out under nitrogen atmosphere under reflux by heating while stirring for 15 hours. After cooling, the reaction product obtained was poured into 100 ml of water and then, extracted with 50 ml of diethyl ether and further with 50 ml of ether. The extracts together were dried and distilled and thus, 8.9 g of 4-fluoro-2',4'-dimethylbenzophenone were obtained.

Workup

  1. additionadded
  2. customwater in the reaction system was removed together with benzene by azeotropy
  3. temperatureunder reflux
  4. temperatureby heating
  5. temperatureAfter cooling
  6. customthe reaction product obtained
  7. extractionextracted with 50 ml of diethyl ether and further with 50 ml of ether
  8. customThe extracts together were dried
  9. distillationdistilled

Sources & evidence

ORD record
ord-88f76edc44844a389177ddba49135135
Source dataset
uspto-grants-1984_06
Patent number
US04453009

Reaction notes

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