2-Chloro-4-(trifluoromethyl)benzonitrile → 2-(Methylthio)-4-(trifluoromethyl)benzonitrile

HRID 1634624Notes

Reaction equation

[CH3:1][S-:2].[Na+].Cl[C:5]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:6]=1[C:7]#[N:8]>CC(C)=O>[CH3:1][S:2][C:5]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:6]=1[C:7]#[N:8]

Participants

Conditions

Temperature: 32.5 °C

Procedure

Sodium thiomethoxide (37 g of a 21% aqueous solution, 0.11M) was added during 2 hours to a solution of 2-chloro-4-trifluoromethylbenzonitrile (20.56 g, 0.099M) in acetone (34 g) with stirring at 30-35° C. After a further 2.5 hours at 30-35° C. and 3 hours at 60° C., a further addition of sodium thiomethoxide (3.4 g of a 21% aqueous solution, 0.01M) was made. The mixture was maintained at 60° C. for 2 hours, cooled and the organic phase evaporated to give 2-methylthio-4-trifluoromethylbenzonitrile (20.3 g), m.p.80° C. The yield of product was 91%, with a purity of 97%.

Workup

temperatureThe mixture was maintained at 60° C. for 2 hours
temperaturecooled
customthe organic phase evaporated

Sources & evidence

ORD record: ord-82fb13002ed747fe82c06f83ec242b53
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06506926B1

Reaction notes

Loading…