Boron tribromide → 2-[4-(3-Chlorophenyl)butyl]phenol

HRID 743401Notes

Reaction equation

HRID 743401 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=1)C1C=CC=CC=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:25][C:21]1[CH:20]=[C:19]([CH2:18][CH2:17][CH2:16][CH2:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[OH:8])[CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 194240571-(2-Benzyloxyphenyl)-4-(3-chlorophenyl)butane

Product 1

HCID 194238562-[4-(3-Chlorophenyl)butyl]phenolYield 80.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Following a procedure similar to that described in the final part of Preparation 15, a solution of 3.04 g of this 1-(2-benzyloxyphenyl)-4-(3-chlorophenyl)butane in 18 ml of methylene chloride was treated with 8.67 ml of a 1M solution of boron tribromide in methylene chloride to eliminate the benzyl group. The resulting crude product 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 1.82 g (yield 80%) of the title compound as a colorless oil.

Workup

  1. custompart of Preparation 15
  2. customThe resulting crude product was purified by column chromatography through silica gel
  3. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-1852bf7c39454fe7ad585c2889131b87
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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