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

HRID 361901Notes

Reaction equation

HRID 361901 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)methyltriphenylphosponium 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-57a1aa3487964c4ba41d98c5f42871b4
Source dataset
uspto-grants-1999_02
Patent number
US05866577

Reaction notes

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