4-Methoxybenzaldehyde → 5-Bromo-2-[2-(4-methoxyphenyl)vinyl]benzofuran

HRID 53967Notes

Reaction equation

HRID 53967 reaction equation
[Cl-].[Br:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH2:11][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:8][C:7]=2[CH:31]=1.[CH:32](=O)[C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=1.C1CCN2C(=NCCC2)CC1>O1CCCC1.C(O)C>[Br:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH:11]=[CH:32][C:33]3[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=3)=[CH:8][C:7]=2[CH:31]=1

Participants

6

Reactant 3

HCID 312444-MethoxybenzaldehydeHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 21844513(5-Bromo-2-benzofuranyl)methyltriphenylphosphonium chloride

Product 1

HCID 537809305-Bromo-2-[2-(4-methoxyphenyl)vinyl]benzofuranYield 55.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

91.5 g of (5-bromo-2-benzofuranyl)methyltriphenylphosphonium chloride and 25 g of p-anisaldehyde were dissolved in a mixture solvent of 180 ml of tetrahydrofuran and 180 ml of ethanol. With stirring at room temperature, 27.58 g of 1,8-diazabicyclo[5.4.0]-7-undecene was added to the above solution, and the mixture was stirred for 18 hours. Thereafter, the reaction solution was concentrated to collect precipitated crystals by filtration, thereby obtaining 32.8 g of 5-bromo-2-[2-(4-methoxyphenyl)vinyl]benzofuran as one of the stereoisomers.

Workup

  1. stirringthe mixture was stirred for 18 hours
  2. concentrationThereafter, the reaction solution was concentrated
  3. customto collect
  4. customprecipitated crystals
  5. filtrationby filtration

Sources & evidence

ORD record
ord-00f938796aad4e31a0f87288ee949c32
Source dataset
uspto-grants-1997_04
Patent number
US05620991

Reaction notes

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