Bromine → (S)-(+)-5-Bromo-2-(2-methylbutyloxy)benzonitrile

HRID 1250332Notes

Reaction equation

HRID 1250332 reaction equation
[CH3:1][C@@H:2]([CH2:13][CH3:14])[CH2:3][O:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[C:7]#[N:8].[Br:15]Br>C(Cl)(Cl)Cl>[Br:15][C:10]1[CH:11]=[CH:12][C:5]([O:4][CH2:3][C@@H:2]([CH3:1])[CH2:13][CH3:14])=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

4

Reactant 2

HCID 24408Bromine2×HCID 53752700(S)-(+)-2-(2-Methylbutyloxy)benzonitrile

Product 1

HCID 53787839(S)-(+)-5-Bromo-2-(2-methylbutyloxy)benzonitrile

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of compound 39 (4.25 g, 0.022 mol), bromine (12.31 g, 0.077 mol) and chloroform (50 ml) was heated under reflux overnight. A further portion of bromine (12.31 g, 0.077 mol) was then added and heating continued for another 24 h. The resultant solution was washed with a saturated solution of sodium thiosulphate and finally with water. The dichloromethane solution was dried (MgSO4) and evaporated in vacuo and the crude oil was purified by column chromatography (10% petrol/dichloromethane) to yield a fawn oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. temperatureheating
  4. washThe resultant solution was washed with a saturated solution of sodium thiosulphate and finally with water
  5. dry with materialThe dichloromethane solution was dried (MgSO4)
  6. customevaporated in vacuo
  7. customthe crude oil was purified by column chromatography (10% petrol/dichloromethane)
  8. customto yield a fawn oil

Sources & evidence

ORD record
ord-8d30123973814434a2565ff79d56d396
Source dataset
uspto-grants-2002_01
Patent number
US06337420B1

Reaction notes

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