Thiophenol → 2,4,5-Trifluoro-6-phenylthioisophthalonitrile
Reaction equation
F[C:2]1[C:7]([C:8]#[N:9])=[C:6]([F:10])[C:5]([C:11]#[N:12])=[C:4]([F:13])[C:3]=1[F:14].[F-].[K+].[C:17]1([SH:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(#N)C>[F:10][C:6]1[C:5]([C:11]#[N:12])=[C:4]([F:13])[C:3]([F:14])=[C:2]([S:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:7]=1[C:8]#[N:9]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A 2.0 g amount of tetrafluoroisophthalonitrile and 0.87 g of potassium fluoride were dissolved in 10 ml of acetonitrile. After cooling the mixture to a temperature of 0° C. by an ice-water bath, 1.1 g of phenyl mercaptan was dropwise added by a syringe. While mixture was maintained at a temperature of about 0° C., the mixture was stirred for 8 hours and the solvent was then distilled off. A 50 ml amount of water was added to the mixture and potassium fluoride was dissolved. The mixture was extracted with chloroform, and the extract was dried with magnesium sulfate. The chloroform was distilled off in vacuo and the resultant liquid was then distilled in vacuo to obtain 1.8 g (63% yield) of the desired compound No. 41 at a boiling point of 65° C. to 67° C./0.7 mmHg.
Workup
- temperatureWhile mixture was maintained at a temperature of about 0° C.
- distillationthe solvent was then distilled off
- additionA 50 ml amount of water was added to the mixture and potassium fluoride
- dissolutionwas dissolved
- extractionThe mixture was extracted with chloroform
- dry with materialthe extract was dried with magnesium sulfate
- distillationThe chloroform was distilled off in vacuo
- distillationthe resultant liquid was then distilled in vacuo
Sources & evidence
- ORD record
- ord-e78c1622567544b08df3601068511f5d
- Source dataset
- uspto-grants-1986_09
- Patent number
- US04614742
Reaction notes
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