Water → 2-Cyano-2-(3-phenoxyphenyl)hexyl bromide

HRID 1863003Notes

Reaction equation

HRID 1863003 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:14]([CH2:17][CH2:18][CH2:19][CH3:20])[C:15]#[N:16])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:21][CH2:22]Br.[OH-].[Na+].O>CS(C)=O>[C:15]([C:14]([C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:9]=1)([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:22][Br:21])#[N:16]

Participants

6

Reactant 4

HCID 962WaterHCID 3024DibromomethaneHCID 14798Sodium HydroxideHCID 234689332-(3-Phenoxyphenyl)hexanenitrile

Product 1

HCID 234689502-Cyano-2-(3-phenoxyphenyl)hexyl bromideYield 88.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 10 g (0.038 mole) of 2-(3-phenoxyphenyl) hexanenitrile, 6.6 g (0.038 mole) of dibromomethane in 50 ml of dimethyl sulfoxide is added 3.2 g (0.04 mole) of 50% sodium hydroxide solution dropwise. The reaction mixture is stirred at 60° for one hour, poured into water and extracted with ether. The combined ether extracts are washed with water and dried over MgSO4. Solvent is evaporated to give 12 g of product.

Workup

  1. extractionextracted with ether
  2. washThe combined ether extracts are washed with water
  3. dry with materialdried over MgSO4
  4. customSolvent is evaporated

Sources & evidence

ORD record
ord-d0c8dc9138ac4d0491fe01680600d91e
Source dataset
uspto-grants-1979_09
Patent number
US04167576

Reaction notes

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