Allyl bromide → α-2-Propen-1-ylbenzeneacetonitrile

HRID 1436872Notes

Reaction equation

HRID 1436872 reaction equation
[CH2:1]([C:8]#[N:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH2:20](Br)[CH:21]=[CH2:22]>C1COCC1>[C:8]([CH:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:22][CH:21]=[CH2:20])#[N:9]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 8794PhenylacetonitrileHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 10607021α-2-Propen-1-ylbenzeneacetonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled solution (−78° C.) of benzyl cyanide (5.00 g, 42.7 mmol) in anhydrous THF was added LiHMDS (1M in THF, 46.9 mL, 46.9 mmol) dropwise. After 0.5 hour, allyl bromide (5.16 g, 42.6 mmol) was added dropwise to the reaction mixture. The reaction mixture was warmed to room temperature, and the solvent was removed under vacuum. The residual material was purified using silica gel column chromatography eluting with 100% hexanes. The appropriate fractions were combined and concentrated to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ 7.44 (m, 5H), 5.81 (m, 1H), 5.12 (m, 2H), 4.35 (t, J=6.9 Hz, 1H), 2.61 (m, 2H) ppm. ES MS M+1=158.

Workup

  1. customthe solvent was removed under vacuum
  2. customThe residual material was purified
  3. washeluting with 100% hexanes
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-594c01fdd42d49e884db7c14e1c8fc52
Source dataset
uspto-grants-2009_11
Patent number
US07619086B2

Reaction notes

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