4-(4-Chlorobenzoyl)benzyl bromide → 4-Chloro-4'-methylthiomethylbenzophenone

HRID 2099Notes

Reaction equation

HRID 2099 reaction equation
Br[CH2:2][C:3]1[CH:17]=[CH:16][C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1.[CH3:18][SH:19].[Na]>CO>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([C:7]([C:6]2[CH:16]=[CH:17][C:3]([CH2:2][S:19][CH3:18])=[CH:4][CH:5]=2)=[O:8])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 98396514-(4-Chlorobenzoyl)benzyl bromideHCID 45051789Methylmercaptan sodium

Product 1

HCID 196893654-Chloro-4'-methylthiomethylbenzophenoneYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-bromomethyl-4'-chlorobenzophenone (3.1 g) and 15% methylmercaptan-sodium aqueous solution (5.6 g) were added to methanol (150 ml), and the mixture was stirred for 30 minutes under reflux. The reaction mixture was concentrated and extracted with ethyl acetate. The ethyl acetate layer was washed with water and then dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure. The residual solid was washed with n-hexane to obtain the desired product (2.3 g, melting point: 59° to 61° C., yield: 83%).

Workup

  1. temperatureunder reflux
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationEthyl acetate was distilled off under reduced pressure
  7. washThe residual solid was washed with n-hexane

Sources & evidence

ORD record
ord-f13ed1df908340769124c76cde4ad555
Source dataset
uspto-grants-1998_03
Patent number
US05728699

Reaction notes

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