(3-Bromopropyl)benzene → HCID 12222179, compound

HRID 1708141Notes

Reaction equation

HRID 1708141 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].CC(C)([O-])C.[K+].Br[CH2:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O>[C:20]1([CH2:19][CH2:18][CH2:17][O:9][C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 12503(3-Bromopropyl)benzeneHCID 130194-CyanophenolHCID 23665647Potassium tert-butoxide

Product 1

HCID 12222179HCID 12222179, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

There was dissolved 3.574 g of p-cyanophenol in 30 ml of N,N-dimethylformamide, followed by addition of 4.364 g of a 90% potassium t-butoxide and stirring at room temperature for 30 minutes. Then 6.570 g of 1-bromo-3-phenylpropane was dropwise added to the solution and the mixture was stirred for 20 hours. The reaction solution was added to ice water, the resulting precipitates were filtered off, washed with water and recrystallized from a mixture of ethanol and n-hexane to give 5.176 g (yield 72.7%) of 4-(3-phenylpropoxy)benzonitrile.

Workup

  1. stirringthe mixture was stirred for 20 hours
  2. customthe resulting precipitates
  3. filtrationwere filtered off
  4. washwashed with water
  5. customrecrystallized from a mixture of ethanol and n-hexane

Sources & evidence

ORD record
ord-77b8250ac3a84427bc3b35c69fd5b3c1
Source dataset
uspto-grants-1994_10
Patent number
US05356916

Reaction notes

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