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Dimethylformamide → 4-Chloro-4'-methylsulfonylmethylbenzophenone

HRID 2096
Notes
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Reaction equation

HRID 2096 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][S:19]([O-:21])=[O:20].[Na+].CN(C)C=O>O>[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])(=[O:21])=[O:20])=[CH:4][CH:5]=2)=[O:8])=[CH:10][CH:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 2733271Sodium methanesulfinateHCID 98396514-(4-Chlorobenzoyl)benzyl bromide

Product 1

HCID 187799134-Chloro-4'-methylsulfonylmethylbenzophenoneYield 90.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-bromomethyl-4'-chlorobenzophenone (3.1 g) and sodium methanesulfinate (1.5 g) were added to N,N-dimethylformamide (50 ml), and the mixture was stirred for 16 hours at room temperature. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and 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 (2.8 g, melting point: 164° to 166° C., yield: 90%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationEthyl acetate was distilled off under reduced pressure
  5. washThe residual solid was washed with n-hexane

Sources & evidence

ORD record
ord-ade4f0eddda041248b4ac3c87079d5f2
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05728699

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes