Ethyl Bromide → 4-Chloro-4'-ethylthiomethylbenzophenone

HRID 2097

Reaction equation

HRID 2097 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][SH:15])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[CH2:18](Br)[CH3:19].[OH-].[K+]>CO>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][S:15][CH2:18][CH3:19])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 14797Potassium HydroxideHCID 196893804-Chloro-4'-mercaptomethylbenzophenone

Product 1

HCID 196893544-Chloro-4'-ethylthiomethylbenzophenoneYield 79.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-chloro-4'-mercaptomethylbenzophenone (16.0 g), ethyl bromide (7.4 g) and potassium hydroxide (4.3 g) were added to methanol (250 ml), and the mixture was stirred for 30 minutes under reflux. The reaction mixture was cooled to room temperature and then concentrated. Water was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and then dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1) to obtain the desired product 14.0 g, melting point: 33° to 34° C., yield: 79%).

Workup

  1. temperatureunder reflux
  2. concentrationconcentrated
  3. additionWater was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-854622046616431a8dec648c46bb4905
Source dataset
uspto-grants-1998_03
Patent number
US05728699

Linked notes

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