Methane → 2-(3-Chlorophenylthio)benzoic acid

反応式

[C:1](=[O:4])([O-])[O-:2].[K+].[K+].Br[C:8]1[CH:9]=[C:10]([Cl:14])[CH:11]=[CH:12][CH:13]=1.O.[CH4:16].C[S:18]([CH3:20])=O>>[Cl:14][C:10]1[CH:9]=[C:8]([S:18][C:20]2[CH:12]=[CH:13][CH:8]=[CH:9][C:16]=2[C:1]([OH:2])=[O:4])[CH:13]=[CH:12][CH:11]=1

参加物

反応物 5

HCID 297Methane

HCID 679Dimethyl Sulfoxide

HCID 962Water

HCID 79281-Bromo-3-chlorobenzene

HCID 11430Potassium Carbonate

生成物 1

HCID 834292-(3-Chlorophenylthio)benzoic acid収率 85%

実験手順

A mixture of thiosolicyclic acid (50.14 g. 0.33 mol) and cupric acetate (5.0 g) in DMSO (500 mL) was brought to reflux and potassium carbonate (54.3 g) was added in portion. 3-Bromochlorobenzene (42 mL, 0.36 mol) was then added via syringe and the mixture was refluxed for 3 hours. The reaction mixture was poured into water, treated with charcoal and filtered through celite. The filtrate was acidified with concentrated HCl and the precipitate which formed was collected by filtration, washed with water and dried in vacuo at 60° C. to afford 75.01 g (85%) of 2-[(3-chlorophenyl)thio]benzoic acid.