Water → HCID 71117360, compound

HRID 2368494Notes

Reaction equation

HRID 2368494 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:11](#[N:15])[CH:12]([CH3:14])[CH3:13].[F:16][C:17]1[C:24]([F:25])=[CH:23][CH:22]=[C:21]([F:26])[C:18]=1[CH2:19]Br.O>C1COCC1>[CH3:13][C:12]([CH3:14])([CH2:19][C:18]1[C:21]([F:26])=[CH:22][CH:23]=[C:24]([F:25])[C:17]=1[F:16])[C:11]#[N:15]

Participants

6

Reactant 4

HCID 962WaterHCID 6559IsobutyronitrileHCID 5190612,3,6-Trifluorobenzyl bromideHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 71117360HCID 71117360, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium bis(trimethylsilyl)amide (LiHMDS) (1M in THF, 26.6 mL, 26.6 mmol) was added to a solution of isobutyronitrile (2.4 mL, 26.6 mmol) in THF at −78° C. and stirred for 25 minutes. 2,3,6-trifluorobenzyl bromide (2.3 mL, 17.8 mmol) was added and the reaction was warmed to room temperature and stirred for 1.5 h. Water was added to quench the reaction and it was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to yield 2,2-dimethyl-3-(2,3,6-trifluorophenyl)propanenitrile (34) as a white solid.

Workup

  1. stirringstirred for 1.5 h
  2. customto quench
  3. customthe reaction and it
  4. extractionwas extracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a56bbcf73fd540338c3358b72118fc0b
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

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