Water → 2-(1-(Trifluoromethyl)cyclopropyl)acetonitrile

HRID 522725Notes

Reaction equation

HRID 522725 reaction equation
CC1C=CC(S(O[CH2:12][C:13]2([C:16]([F:19])([F:18])[F:17])[CH2:15][CH2:14]2)(=O)=O)=CC=1.[C-:20]#[N:21].[K+].O>CN(C=O)C>[F:19][C:16]([F:17])([F:18])[C:13]1([CH2:12][C:20]#[N:21])[CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 24805800HCID 24805800, compound

Product 1

HCID 847630882-(1-(Trifluoromethyl)cyclopropyl)acetonitrileYield 39.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Treat a solution of (1-(trifluoromethyl)cyclopropyl)methyl 4-methylbenzenesulfonate (12 g, 40.8 mmol) in DMF (150 mL) with potassium cyanide (3.5 g, 53 mmol) and heat at 50-70° C. for 3 days. Treat the mixture with water, extract with EtOAc (3×), wash the combined organics with water, then brine, dry and concentrate under reduced pressure to give the title compound (2.4 g, 39% yield). 1H NMR (400 MHz, CDCl3): δ 2.81 (s, 2H), 1.24-1.18 (m, 2H), 0.95-0.92 (m, 2H).

Workup

  1. extractionextract with EtOAc (3×)
  2. washwash the combined organics with water
  3. dry with materialbrine, dry
  4. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-fbed559a75354f189e1fd328401043c4
Source dataset
uspto-grants-2016_05
Patent number
US09334267B2

Reaction notes

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