Triphenylphosphine → Benzene, 1-(bromomethyl)-3-(phenylmethyl)-

HRID 483737Notes

Reaction equation

HRID 483737 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(Cl)(Br)C(Cl)(Cl)[Br:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(OCC)C>[CH2:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11][Br:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 694261,2-Dibromo-1,1,2,2-tetrachloroethaneHCID 5976133-Benzylbenzyl alcohol

Product 1

HCID 9992801Benzene, 1-(bromomethyl)-3-(phenylmethyl)-Yield 100.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 3-benzylbenzyl alcohol (1.98 g) in diethyl ether (60 cm3) was cooled in an ice bath, and 1,1,2,2-tetrachloro-1,2-dibromoethane (3.90 g) added. When the addition was complete, triphenyl phosphine (3.14 g) was added to the cooled mixture. The reaction mixture was stirred for 10 minutes, then filtered and the solvent evaporated under reduced pressure. The resultant yellow oil was purified by column chromatography on a silica gel support, eluting with petroleum ether (boiling range 60°-80° C.) containing 10% by volume diethyl ether, to give 3-benzylbenzyl bromide (2.62 g).

Workup

  1. additionWhen the addition
  2. filtrationfiltered
  3. customthe solvent evaporated under reduced pressure
  4. customThe resultant yellow oil was purified by column chromatography on a silica gel support
  5. washeluting with petroleum ether (boiling range 60°-80° C.)
  6. additioncontaining 10% by volume diethyl ether

Sources & evidence

ORD record
ord-d28331d7d71145f8847a7e9bd5fcafb3
Source dataset
uspto-grants-1993_07
Patent number
US05225607

Reaction notes

Loading…