Triethylamine → 2-Bromo-4,4,4-trifluorocrotononitrile

HRID 846874Notes

Reaction equation

HRID 846874 reaction equation
C(N(CC)CC)C.[Br:8][CH:9]([CH:12](Br)[C:13]([F:16])([F:15])[F:14])[C:10]#[N:11]>O1CCCC1>[Br:8]/[C:9](=[CH:12]\[C:13]([F:16])([F:15])[F:14])/[C:10]#[N:11]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 109020202,3-Dibromo-4,4,4-trifluorobutyronitrile

Product 1

HCID 218608782-Bromo-4,4,4-trifluorocrotononitrileYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (317 g, 0.037 mol) is added dropwise to a solution of 2,3-dibromo-4,4,4-trifluorobutyronitrile (5.32 g, 0.023 mol) and tetrahydrofuran (100 mL). A voluminous white precipitate forms during the addition. Stirring is continued for 1 hour, then the solid is filtered off and washed with tetrahydrofuran. The tetrahydrofuran is distilled off to give a dark brown oil. Bulb to bulb distillation (15 mm, 24° C.) of the oil yields the title product as a clear colorless liquid (3.1 g, 82%). NMR spectral analyses identifies a 6:1 mixture of E:Z.

Workup

  1. additionA voluminous white precipitate forms during the addition
  2. filtrationthe solid is filtered off
  3. washwashed with tetrahydrofuran
  4. distillationThe tetrahydrofuran is distilled off
  5. customto give a dark brown oil
  6. distillationBulb to bulb distillation (15 mm, 24° C.) of the oil

Sources & evidence

ORD record
ord-241b1391dc854459bc6fb68242ff9f51
Source dataset
uspto-grants-1992_08
Patent number
US05138087

Reaction notes

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