Cesium carbonate → 3-Ethynyl-1,1'-biphenyl

HRID 271109Notes

Reaction equation

HRID 271109 reaction equation
[C:1]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]#[C:8][Si](C)(C)C)[CH:2]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CCO.C(Cl)Cl>[C:7]([C:3]1[CH:2]=[C:1]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=1)#[CH:8]

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 59834575[([1,1'-Biphenyl]-3-yl)ethynyl](trimethyl)silane

Product 1

HCID 127880263-Ethynyl-1,1'-biphenylYield 91%

Reagents, catalysts & solvents 1

HCID 21584144Dichloromethane ethanolSolvent

Procedure

To a solution of (1,1′-biphenyl-3-ylethynyl)(trimethyl)silane (4.74 g, 18.96) in 1/1 EtOH/CH2Cl2 (60 mL) is added Cs2CO3 (6.78 g, 20.85 mmol) at room temperature. After stirring for 1 h, the insoluble material is filtered off and the filtrate is concentrated. The crude material is purified by chromatography (silica gel, 100% hexane) to give the title compound (3.07 g, 91%) as an oil. MS (+) EI: 178 M+.

Workup

  1. filtrationthe insoluble material is filtered off
  2. concentrationthe filtrate is concentrated
  3. customThe crude material is purified by chromatography (silica gel, 100% hexane)

Sources & evidence

ORD record
ord-72224c16d3a64c1ca9e66da71a12be05
Source dataset
uspto-grants-2008_11
Patent number
US07452885B2

Reaction notes

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