Water → 1-[4-(Benzenesulfonyl)phenyl]ethan-1-one

HRID 347287Notes

Reaction equation

HRID 347287 reaction equation
[C:1]1([S:7]([O-:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].[CH3:11][C:12]([C:14]1[CH:19]=[CH:18][C:17](F)=[CH:16][CH:15]=1)=[O:13].O>CS(C)=O>[C:1]1([S:7]([C:17]2[CH:18]=[CH:19][C:14]([C:12](=[O:13])[CH3:11])=[CH:15][CH:16]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 98284'-FluoroacetophenoneHCID 2723840Benzenesulfinic acid, sodium salt

Product 1

HCID 2658781-[4-(Benzenesulfonyl)phenyl]ethan-1-oneYield 87.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Preparation 1 of WO 96/262,196 described the reaction of sodium benzenesulfinate (43 g, 0.26 mol) and 4-fluoroaceto phenone (30 g, 0.22 mol) at 130° C. in dimethyl sulfoxide (200 mL) for 48 hours. The mixture is then poured into 1000 mL of water. The solid formed is colled and dried to give 50 g of 1-(4-phenylsulfonyl-phenyl)-ethanone. This solid is suspended in ethanol (350 mL), heated to 60° C. and treated as described in J. Med. Chem., 34, 3295 (1991) to give 4-phenylsulfonyl benzoic acid melting at 269–271° C. A suspension of 4-phenyl sulfonylbenzoic acid (15 g, 0.57 mol) in toluene (50 mL) is treated with thionyl chloride (25 mL). A few drops of N,N-dimethylformamide are added and the suspension is heated to 70° C. for three hours. The solution is concentrated to give the title intermediate compound which is used without further purification.

Workup

  1. customPreparation 1 of WO 96/262,196
  2. customThe solid formed
  3. customdried

Sources & evidence

ORD record
ord-3d1f277437d34a5488ff4fe064ce05aa
Source dataset
uspto-grants-2007_02
Patent number
US07173128B2

Reaction notes

Loading…