Boron tribromide → HCID 19423921, compound

HRID 743397Notes

Reaction equation

HRID 743397 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21]CC1C=CC=CC=1.B(Br)(Br)Br>C(Cl)Cl>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[OH:21]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 19423941HCID 19423941, compound

Product 1

HCID 19423921HCID 19423921, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

The whole of this 4-(2-naphthyl)-1-(2-benzyloxyphenyl)butane was dissolved in 20 ml of methylene chloride, and 9.5 ml of a 1M solution of boron tribromide in methylene chloride were added, whilst ice-cooling and stirring, to the solution. The resulting mixture was then stirred at the same temperature for 1 hour. At the end of this time, the reaction mixture was diluted with methylene chloride, washed with water, dried over anhydrous sodium sulfate, and concentrated by evaporation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 4:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 1.56 g (yield 78%) of the title compound as colorless solid.

Workup

  1. temperaturecooling
  2. stirringThe resulting mixture was then stirred at the same temperature for 1 hour
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customThe resulting residue was purified by column chromatography through silica gel
  7. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-216fd3656a5c475c8f75e9adc4e3592c
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

Loading…