3-Iodo-4,5-dimethoxybenzoic acid → 3-[(3-Fluorophenyl)ethynyl]-4,5-dimethoxybenzoic acid

HRID 638956Notes

Reaction equation

HRID 638956 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[CH:4]=1)#[CH:2].I[C:11]1[CH:12]=[C:13]([CH:17]=[C:18]([O:22][CH3:23])[C:19]=1[O:20][CH3:21])[C:14]([OH:16])=[O:15]>>[F:9][C:5]1[CH:4]=[C:3]([C:1]#[C:2][C:11]2[CH:12]=[C:13]([CH:17]=[C:18]([O:22][CH3:23])[C:19]=2[O:20][CH3:21])[C:14]([OH:16])=[O:15])[CH:8]=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 2304593-Iodo-4,5-dimethoxybenzoic acidHCID 5202181-Ethynyl-3-fluorobenzene

Product 1

HCID 686861573-[(3-Fluorophenyl)ethynyl]-4,5-dimethoxybenzoic acid

Procedure

3-(3-Fluorophenylethynyl)-4,5-dimethoxybenzoic acid was prepared by coupling 1-ethynyl-3-fluorobenzene with 3-iodo-4,5-dimethoxybenzoic acid Method R. The crude product was purified via flash column chromatography on silica gel (5% MeOH in CH2Cl2 as an eluent) to give 3-(3-fluorophenylethynyl)-4,5-dimethoxybenzoic acid in 95% yield. ESMS: m/z 299.3 [M−H].

Workup

  1. custom3-(3-Fluorophenylethynyl)-4,5-dimethoxybenzoic acid was prepared
  2. customThe crude product was purified via flash column chromatography on silica gel (5% MeOH in CH2Cl2 as an eluent)

Sources & evidence

ORD record
ord-b32646cef7314f0090843736b803e58a
Source dataset
uspto-grants-2010_04
Patent number
US07691843B2

Reaction notes

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