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

HRID 651305Notes

Reaction equation

HRID 651305 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>>[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

3

Reactant 2

HCID 24408BromineHCID 53752700(S)-(+)-2-(2-Methylbutyloxy)benzonitrile

Product 1

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

Procedure

A mixture of compound 39 (4.25 g, 0.-22 mol), 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. additionwas then added
  2. temperatureheating
  3. washThe resultant solution was washed with a saturated solution of sodium thiosulphate and finally with water
  4. dry with materialThe dichloromethane solution was dried (MgSO4)
  5. customevaporated in vacuo
  6. customthe crude oil was purified by column chromatography (10% petrol/dichloromethane)
  7. customto yield a fawn oil

Sources & evidence

ORD record
ord-09d244bbfa50466ca11c62a4415342a0
Source dataset
uspto-grants-2001_08
Patent number
US06278028B1

Reaction notes

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