Phosphorus tribromide → 2,2,5,5-Tetramethyl-1-cyclopentylmethylbromide

HRID 2291009Notes

Reaction equation

HRID 2291009 reaction equation
[CH3:1][C:2]1([CH3:11])[CH2:6][CH2:5][C:4]([CH3:8])([CH3:7])[CH:3]1[CH2:9]O.P(Br)(Br)[Br:13]>C1C=CC=CC=1>[CH3:1][C:2]1([CH3:11])[CH2:6][CH2:5][C:4]([CH3:8])([CH3:7])[CH:3]1[CH2:9][Br:13]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 13629260(2,2,5,5-Tetramethylcyclopentyl)methanol

Product 1

HCID 136292612,2,5,5-Tetramethyl-1-cyclopentylmethylbromide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
0 °C

Procedure

2,2,5,5-Tetramethyl-1-cyclopentylmethanol is dissolved in benzene and stirred at 0° C. under argon. A solution of phosphorus tribromide in benzene is added and the mixture is stirred for 2 hours and then heated to 60° C. for 4 hours. The mixture is cooled, poured into ice and extracted with ether. The organic layer is washed with saturated NaHCO3, dried over MgSO4 and evaporated to yield 2,2,5,5-Tetramethyl-1-cyclopentylmethyl bromide.

Workup

  1. stirringthe mixture is stirred for 2 hours
  2. temperatureheated to 60° C. for 4 hours
  3. temperatureThe mixture is cooled
  4. additionpoured into ice
  5. extractionextracted with ether
  6. washThe organic layer is washed with saturated NaHCO3
  7. dry with materialdried over MgSO4
  8. customevaporated

Sources & evidence

ORD record
ord-34291b046df54d79ac2e382d7dd92b86
Source dataset
uspto-grants-1986_10
Patent number
US04619834

Reaction notes

Loading…