4-(4-Iodophenyl)benzonitrile → 4'-Mercaptobiphenyl-4-carbonitrile

HRID 6015

Reaction equation

I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C[S-:17].[Na+]>CN(C)P(N(C)C)(N(C)C)=O>[SH:17][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

3.25 g (10.8.10-3 mol) of 4-(4-iodophenyl)benzonitrile are dissolved in 50 ml of hexamethylphosphoramide, and 3.05 g (43.4.10-3 mol) of sodium thiomethylate are then added to the solution. The reaction mixture is heated at 100° C. for 1.5 hours and then, after cooling, hydrolyzed in a 1 N hydrochloric acid/ice mixture. The expected product is extracted with ethyl acetate. The resulting organic phase is washed with water until the pH of the washings is neutral, dried over magnesium sulfate and then evaporated under reduced pressure to give 2.4 g (quantitative yield) of a pale yellow solid.

Workup

extractionThe expected product is extracted with ethyl acetate
washThe resulting organic phase is washed with water until the pH of the washings
dry with materialdried over magnesium sulfate
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-b40073ab084446aca3ddff0719ca2133
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05246961

Linked notes

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