Butyl bromide → HCID 68487335, compound

HRID 2170249Notes

Reaction equation

HRID 2170249 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[CH3:8].C([O-])([O-])=O.[K+].[K+].Br[CH2:19][CH2:20][CH2:21][CH3:22]>CC(C)=O>[CH2:19]([O:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[CH3:8])[CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 18440061HCID 18440061, compound

Product 1

HCID 68487335HCID 68487335, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of (3-hydroxy-4-methylphenyl)-acetonitrile (1.7 g, 11.5 mmol) in acetone (100 ml), K2CO3 (7.9 g, 57.5 mmol) and 1-bromo butane (6.1 ml, 57.5 mmol) were added. The suspension was refluxed for 24 h and the solvent was evaporated under reduced pressure. The residue was dissolved in CH2Cl2 and washed with water and brine. The organic layer was dried over Na2SO4, filtered and the solvent evaporated under reduced pressure. The crude was purified by flash chromatography (petroleum ether:EtOAc 9.5:0.5) affording the title compound (1.43 g, 61% yield) as colourless oil.

Workup

  1. temperatureThe suspension was refluxed for 24 h
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. washwashed with water and brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent evaporated under reduced pressure
  8. customThe crude was purified by flash chromatography (petroleum ether:EtOAc 9.5:0.5)

Sources & evidence

ORD record
ord-1f7eccfeafad4eb1bf2fff74df76d8e8
Source dataset
uspto-grants-2015_06
Patent number
US09051240B2

Reaction notes

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