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

HRID 361904Notes

Reaction equation

HRID 361904 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH:10]=[CH:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[CH:7][C:6]=2[CH:20]=1>O1CCCC1.C(O)C.[Pt](=O)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[CH:7][C:6]=2[CH:20]=1

Participants

5

Reactant 1

HCID 537809305-Bromo-2-[2-(4-methoxyphenyl)vinyl]benzofuran

Product 1

HCID 218443105-Bromo-2-[2-(4-methoxyphenyl)ethyl]benzofuranYield 75.4%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

128 g of 5-bromo-2-[2-(4-methoxyphenyl)-vinyl]benzofuran as a mixture of two stereoisomers was dissolved in a solvent mixture of 1.3 1 of tetrahydrofuran and 0.7 l of ethanol. The resulting solution was mixed with 3.0 g of platinum dioxide and subjected to 4 hours of catalytic hydrogenation under normal pressure. Thereafter, the catalyst was removed by filtration, the resulting filtrate was concentrated, and crystals thus precipitated were collected by filtration and washed with ethanol. In this way, 97.08 g of 5-bromo-2-[2-(4-methoxyphenyl)ethyl]-benzofuran was obtained.

Workup

  1. customThereafter, the catalyst was removed by filtration
  2. concentrationthe resulting filtrate was concentrated
  3. customcrystals thus precipitated
  4. filtrationwere collected by filtration
  5. washwashed with ethanol

Sources & evidence

ORD record
ord-ec13e76de6be4667835f553f6a5c94eb
Source dataset
uspto-grants-1999_02
Patent number
US05866577

Reaction notes

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