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

HRID 1614456Notes

Reaction equation

HRID 1614456 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-12a0baff584a48c8be0161fd8475c247
Source dataset
uspto-grants-1993_03
Patent number
US05196610

Reaction notes

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