Boron tribromide → HCID 10537566, compound

HRID 743412Notes

Reaction equation

HRID 743412 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16]CC2C=CC=CC=2)[CH:5]=[CH:6][CH:7]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[OH:16])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 19423963HCID 19423963, compound

Product 1

HCID 10537566HCID 10537566, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The whole of this benzyl 2-[2-(3-chlorophenyl)ethyl]phenyl ether was dissolved in 50 ml of methylene chloride, and 17 ml of a 1M solution of boron tribromide in methylene chloride were added to the solution, whilst ice-cooling. The mixture was then allowed to stand at room temperature for 2 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 10:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 3.80 g (yield 99%) of the title compound as a solid.

Workup

  1. temperaturecooling
  2. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  3. customthe resulting residue was purified by column chromatography through silica gel
  4. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-6bd9165c87b6499482fe8e4aa626d5a9
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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