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

HRID 2118471Notes

Reaction equation

HRID 2118471 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-Tetramethylcyclopentane-1-carboxaldehyde is dissolved in 95% ethanol and sodium borohydride is added. After 24 hours, the reaction is quenched with 1M HCl and extracted with ether. The extract is washed, dried over MgSO4 and evaporated to yield 2,2,5,5-tetramethyl-1-cyclopentylmethanol. 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 and 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
  7. dry with materialsaturated NaHCO3, dried over MgSO4
  8. customevaporated

Sources & evidence

ORD record
ord-e69611995ac74e3daf84046fef6c2b6f
Source dataset
uspto-grants-1987_07
Patent number
US04678675

Reaction notes

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