Phosphorus pentabromide → 1-(2-Bromoethyl)adamantane

HRID 1249811Notes

Reaction equation

HRID 1249811 reaction equation
O[CH2:2][CH2:3][C:4]12[CH2:13][CH:8]3[CH2:9][CH:10]([CH2:12][CH:6]([CH2:7]3)[CH2:5]1)[CH2:11]2.P(Br)(Br)(Br)(Br)[Br:15]>C(OCC)C>[Br:15][CH2:2][CH2:3][C:4]12[CH2:13][CH:8]3[CH2:9][CH:10]([CH2:12][CH:6]([CH2:7]3)[CH2:5]1)[CH2:11]2

Participants

4

Reactant 2

HCID 62678Phosphorus pentabromideHCID 1108102-(Tricyclo(3.3.1.1'3,7)dec-1-yl)ethanol

Product 1

HCID 14163051-(2-Bromoethyl)adamantane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1-Hydroxy-2-(adamant-1-yl)ethane (901.0 mg, 5.0 mmol) was treated with phosphorus pentabromide(3.0 gm, 7.0 mmol) in diethyl ether and warmed slightly until a noticeable exotherm was observed. The resulting red solution was washed with aqueous sodium bicarbonate solution and dried (Na2SO4). Solvent removal gave crude 1-Bromo-2-(adamant-1-yl)ethane. The material was used as is without further purification.

Workup

  1. temperaturewarmed slightly until a noticeable exotherm
  2. washThe resulting red solution was washed with aqueous sodium bicarbonate solution
  3. dry with materialdried (Na2SO4)
  4. customSolvent removal

Sources & evidence

ORD record
ord-d263aac3371748c98cb03507153df8b8
Source dataset
uspto-grants-2002_01
Patent number
US06335343B1

Reaction notes

Loading…