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

HRID 1862997Notes

Reaction equation

HRID 1862997 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-e0c95b3102574855a1e2ee9491436efa
Source dataset
uspto-grants-1979_09
Patent number
US04167576

Reaction notes

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