Dimethyl Sulfoxide → 2-Cyano-2-(2-phenoxyphenyl)hexyl bromide

HRID 128223Notes

Reaction equation

HRID 128223 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH:14]([CH2:17][CH2:18][CH2:19][CH3:20])[C:15]#[N:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:21][CH2:22]Br.CS(C)=O.[OH-].[Na+]>O>[C:15]([C:14]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[O:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:22][Br:21])#[N:16]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 3024DibromomethaneHCID 14798Sodium HydroxideHCID 197756142-(2-Phenoxyphenyl)hexanenitrile

Product 1

HCID 234689402-Cyano-2-(2-phenoxyphenyl)hexyl bromideYield 82.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a three-necked 300 ml round bottom flask are charged 10 g (0.038 mole) of 2-(2-phenoxyphenyl)hexanenitrile, 6.6 g (0.038 mole) of dibromomethane and 50 ml of dimethyl sulfoxide. To this mixture with stirring is added 3.2 g (0.04 mole) of 50% sodium hydroxide solution dropwise. Reaction mixture is heated to give 60° for two hours and then poured into water and extracted with hexane. Combined hexane extracts are washed with water and dried over MgSO4. Solvent is evaporated under vacuum to give 11.2 g of product.

Workup

  1. customReaction mixture
  2. temperatureis heated
  3. customto give 60° for two hours
  4. extractionextracted with hexane
  5. washCombined hexane extracts are washed with water
  6. dry with materialdried over MgSO4
  7. customSolvent is evaporated under vacuum

Sources & evidence

ORD record
ord-a04fc54f54674e53baa7f7023a3030e8
Source dataset
uspto-grants-1981_03
Patent number
US04259339

Reaction notes

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