Acetone → 3-[4-(Bromomethyl)phenyl]2-phenylpropanonitrile

HRID 2255571Notes

Reaction equation

HRID 2255571 reaction equation
[Si](O[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:18]#[N:19])=[CH:12][CH:11]=1)(C(C)(C)C)(C)C.C(Br)(Br)(Br)[Br:27].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)=O>C(#N)C>[Br:27][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:18]#[N:19])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 193856503-[4-(Tert-butyldimethylsilyloxymethyl)phenyl]-2-phenylpropanonitrile

Product 1

HCID 193855943-[4-(Bromomethyl)phenyl]2-phenylpropanonitrileYield 45%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of 1.5 g (4.27 mmol) of the product of Step C dissolved in 20 mL of acetonitrile, was added 2.12 g (6.4 mmol) of carbon tetrabromide, and 1.68 g (6.40 mmol) of triphenylphosphine. The reaction mixture was stirred 30 minutes at 0° C., then allowed to warm to room temperature and 0.5 mL (6.4 mmol) of acetone was added. The reaction mixture was stirred an additional 16 hours at room temperature, then filtered and evaporated in vacuo. The residue was purified on a silica gel flash chromatography column eluted with 5% ethyl acetate/hexane to afford 0.575 g (45%) of the title compound.

Workup

  1. temperatureto warm to room temperature
  2. stirringThe reaction mixture was stirred an additional 16 hours at room temperature
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified on a silica gel flash chromatography column
  6. washeluted with 5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-9164cf9c7bac4ac5b0fb1a755c16164e
Source dataset
uspto-grants-1993_08
Patent number
US05240938

Reaction notes

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