Diethyl Ether → HCID 20343275, compound

HRID 1447914Notes

Reaction equation

HRID 1447914 reaction equation
[C-:1]#[N:2].[K+].[F:4][C:5]([F:18])([O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Br)=[CH:12][CH:11]=1)[CH:6]([F:8])[F:7].CCOCC>O>[F:4][C:5]([F:18])([O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][C:1]#[N:2])=[CH:12][CH:11]=1)[CH:6]([F:8])[F:7]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 9032Potassium CyanideHCID 222617841-(Bromomethyl)-4-(1,1,2,2-tetrafluoroethoxy)benzene

Product 1

HCID 20343275HCID 20343275, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Over a period of 40 minutes, a hot solution of 75.1 g (1.15 mol) of potassium cyanide in 140 ml of water is added to a mechanically stirred 75° C. solution of 160.99 g (0.561 mol) of p-(1,1,2,2-tetrafluoroethoxy)benzyl bromide and 500 ml of anhydrous 2B alcohol. The resulting mixture is refluxed for 1.75 hours. After sitting overnight the reaction mixture is poured into 500 ml of cold water and 400 ml of ether. The combined ether solutions are washed twice with 500 ml of water, dried with sodium sulfate, filtered, and then evaporated on a rotary evaporator to give 114.95 g of an oil. A vacuum distillation of this oil gives, as one distillation fraction, 37.10 g (28%) of the nitrile, boiling point 85° C. to 100° C. at 0.29 mm Hg.

Workup

  1. temperatureThe resulting mixture is refluxed for 1.75 hours
  2. waitAfter sitting overnight
  3. washThe combined ether solutions are washed twice with 500 ml of water
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated on a rotary evaporator

Sources & evidence

ORD record
ord-76ff559352664e99bd0c3899dfc1ad52
Source dataset
uspto-grants-1979_12
Patent number
US04178460

Reaction notes

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