Carbon tetrabromide → 1-Bromo-4-phenylbutane

HRID 2249041Notes

Reaction equation

HRID 2249041 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Br)(Br)(Br)[Br:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:13][CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 76889Benzenebutanol

Product 1

HCID 2596681-Bromo-4-phenylbutaneYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

15.0 g (0.1 mol) 4-phenylbutanol and 39.8 g (0.12 mol) carbontetrabromide were dissolved in 500 ml dry dichloromethane and cooled to 0° C., 36.7 g (0.14 mol) triphenylphosphine was then added and the mixture stirred 1.5 hours under argon at 0° C. then evaporated in vacuo. The resulting mixture was stirred in ether-hexane (1:1) and filtered to remove insoluble material. The filtrate was then passed through a pad of silica gel and concentrated to give a pale yellow liquid 21.3 g.

Workup

  1. customthen evaporated in vacuo
  2. stirringThe resulting mixture was stirred in ether-hexane (1:1)
  3. filtrationfiltered
  4. customto remove insoluble material
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5aa86fbb60754ddb938809c22782c10c
Source dataset
uspto-grants-1991_08
Patent number
US05041638

Reaction notes

Loading…