DCM MeOH AcOH → 3-([1,1'-Biphenyl]-4-YL)propiolic acid

HRID 735083Notes

Reaction equation

HRID 735083 reaction equation
[C:1]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][C:4]([CH:7](Br)C(Br)CC(O)=O)=[CH:3][CH:2]=1.ClCCl.CO.[C:26]([OH:29])(=[O:28])[CH3:27]>>[C:1]1([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:2]=[CH:3][C:4]([C:7]#[C:27][C:26]([OH:29])=[O:28])=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 21877243DCM MeOH AcOHHCID 688160273-Biphenyl-4-yl-2,3-dibromopropanecarboxylic acid

Product 1

HCID 654541843-([1,1'-Biphenyl]-4-YL)propiolic acid

Procedure

Prepared analogously to Example 3.4.b. from 3-biphenyl-4-yl-2,3-dibromopropanecarboxylic acid. Yield: 2.8 g (96.8% of theory); C15H10O2 (M=222.24); melting point: 170° C.; calc.: molecular ion peak (M+H)+: 223; found: molecular ion peak (M+H)+: 223; Rf value: 0.4 (silica gel, dichloromethane/methanol/acetic acid (90:10:1)).

Workup

  1. customPrepared analogously to Example 3.4.b

Sources & evidence

ORD record
ord-2e8bb6f47a574f6cb64b5174bfc4edde
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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