Bromoform → 5-(2'2'-Dibromo-3'3'-dimethylcyclopropyl)-3-methyl-1-pentyn-3-ol

HRID 1196173

Reaction equation

HRID 1196173 reaction equation
[CH3:1][C:2]([CH3:11])=[CH:3][CH2:4][CH2:5][C:6]([OH:10])([C:8]#[CH:9])[CH3:7].[CH:12]([Br:15])(Br)[Br:13].[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[Br:13][C:12]1([Br:15])[C:2]([CH3:1])([CH3:11])[CH:3]1[CH2:4][CH2:5][C:6]([CH3:7])([OH:10])[C:8]#[CH:9]

Participants

5

Reactant 3

HCID 5558Bromoform2×HCID 14798Sodium HydroxideHCID 62842Dehydrolinalool

Product 1

HCID 538034755-(2'2'-Dibromo-3'3'-dimethylcyclopropyl)-3-methyl-1-pentyn-3-olYield 84.5%

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst2×

Procedure

Dehydrolinalool (60.8 g, 0.4 mol), bromoform (151.6 g, 0.6 mol) and 0.8 g of triethylbenzylammonium chloride are placed in a reaction flask and 64 g of a 50% sodium hydroxide solution are added during 30 minutes. The reaction is exothermic and the mixture is therefore cooled with ice. After stirring the mixture at room temperature for 21.5 hours the same amounts of bromoform and triethylbenzylammonium chloride are again added. The reaction becomes exothermic and is cooled with ice. The mixture is left to react at 0° for a further 4 hours, poured onto ice and extracted with methylene chloride. The organic phases are washed neutral, dried and evaporated. In this manner there are obtained 109.5 g (84%) of 5-(2'2'-dibromo-3'3'-dimethylcyclopropyl)-3-methyl-1-pentyn-3-ol.

Workup

  1. temperaturethe mixture is therefore cooled with ice
  2. additionare again added
  3. temperatureis cooled with ice
  4. waitThe mixture is left
  5. customto react at 0° for a further 4 hours
  6. additionpoured onto ice
  7. extractionextracted with methylene chloride
  8. washThe organic phases are washed neutral
  9. customdried
  10. customevaporated

Sources & evidence

ORD record
ord-d0890348fa134590832f593206ada504
Source dataset
uspto-grants-1992_05
Patent number
US05113021

Linked notes

Loading…