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

HRID 256260Notes

Reaction equation

HRID 256260 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-8f5c7ca86a8d4e16bbf58dd1f06bcea2
Source dataset
uspto-grants-1987_10
Patent number
US04701552

Reaction notes

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