Water → HCID 66791018, compound

HRID 1171886Notes

Reaction equation

HRID 1171886 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]([CH2:14][CH2:15]O)[CH:3]=1.P(Br)(Br)[Br:18].O>C1(C)C=CC=CC=1>[Br:18][CH2:15][CH2:14][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 11601085HCID 11601085, compound

Product 1

HCID 66791018HCID 66791018, compoundYield 119.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution, maintained at 5° C., of 710 mg (3.05 mmol) of 2-(4-chlorobiphenyl-2-yl)ethanol, prepared in Example 51, in 10 ml of toluene are added 97 μl (1.02 mmol) of PBr3, and the reaction medium is allowed to return to room temperature. After stirring for 20 hours, the reaction medium is poured into 100 ml of water and extracted with ethyl acetate. The organic phase is washed with water, dried over Na2SO4 and then concentrated under vacuum to give a yellow liquid, which is purified by flash chromatography on a column of silica, in dichloromethane. 360 mg of a pale yellow oil are obtained.

Workup

  1. customto return to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customto give a yellow liquid, which
  7. customis purified by flash chromatography on a column of silica, in dichloromethane

Sources & evidence

ORD record
ord-3cd58f2739a842f1a20e3329d3d56d57
Source dataset
uspto-grants-2010_11
Patent number
US07829721B2

Reaction notes

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