Carbon Dioxide → (3-bromobiphenyl-4-yl)propynoic Acid

HRID 735158Notes

Reaction equation

HRID 735158 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:6][C:7]=1[C:8]#[CH:9].[C:16](=[O:18])=[O:17]>ClCCl.CO>[Br:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:5]=[CH:6][C:7]=1[C:8]#[C:9][C:16]([OH:18])=[O:17]

Participants

4

Reactant 2

HCID 280Carbon DioxideHCID 860607363-Bromo-4-ethynylbiphenyl

Product 1

HCID 68818231(3-bromobiphenyl-4-yl)propynoic Acid

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 4.3.a. from 3-bromo-4-ethynylbiphenyl and carbon dioxide. Yield: 2.5 g (89% of theory); C15H9BrO2 (M=301.13); calc.: molecular ion peak (M+H)+: 301/303 (Br); found: molecular ion peak (M+H)+: 301/303 (Br); Rf value: 0.3 (silica gel, dichloromethane/methanol (90:10)).

Workup

  1. customPrepared analogously to Example 4.3.a

Sources & evidence

ORD record
ord-5bcdda81294b45a1828352c02d91d37c
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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