Ethanol → 2-(Trifluoromethyl)phenylacetonitrile

HRID 1707035Notes

Reaction equation

HRID 1707035 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5]Br.[C-:13]#[N:14].[K+].C(O)C>O>[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][C:13]#[N:14]

Participants

5

Reactant 3

HCID 702EthanolHCID 9032Potassium CyanideHCID 1230571-(Bromomethyl)-2-(trifluoromethyl)benzene

Product 1

HCID 764352-(Trifluoromethyl)phenylacetonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 75 g. (0.31 mole) of o-trifluoromethylbenzyl bromide, 120 g. (0.55 mole) of potassium cyanide, 150 ml. of water and 600 ml. of absolute ethanol is stirred and heated under reflux for 20 hours. The reaction mixture is diluted with 4 liters of water and is extracted with 500 ml. of ether. The extract is dried over anhydrous potassium carbonate and evaporated. Distillation gives 45 g. of the desired product b.p. 103°-105° C./10 mm.

Workup

  1. additionA mixture of 75 g
  2. temperatureheated
  3. temperatureunder reflux for 20 hours
  4. extractionis extracted with 500 ml
  5. dry with materialThe extract is dried over anhydrous potassium carbonate
  6. customevaporated
  7. distillationDistillation
  8. customgives 45 g

Sources & evidence

ORD record
ord-068d7c7ba46249c48f66b4beddca32db
Source dataset
uspto-grants-1980_06
Patent number
US04209621

Reaction notes

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