Carbon tetrabromide → 3-(2,2-Dibromoethenyl)-5-trimethylsilylfuran

HRID 2050647Notes

Reaction equation

HRID 2050647 reaction equation
[CH3:1][Si:2]([CH3:11])([CH3:10])[C:3]1[O:4][CH:5]=[C:6]([CH:8]=O)[CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:31](Br)(Br)([Br:33])[Br:32]>ClCCl>[Br:32][C:31]([Br:33])=[CH:8][C:6]1[CH:7]=[C:3]([Si:2]([CH3:11])([CH3:10])[CH3:1])[O:4][CH:5]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 156632515-(Trimethylsilyl)furan-3-carbaldehyde2×

Product 1

HCID 199915873-(2,2-Dibromoethenyl)-5-trimethylsilylfuran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-trimethylsilyl-4-furaldehyde (Compound 4, 1.0 g, 5.95 mmol) in dichloromethane (2 ml) was added to a solution of triphenylphosphine (3.9 g, 14.9 mmol) and carbon tetrabromide 2.46 g, 7.44 mmol) in dichloromethane (15 ml) at 0° under argon. After 1 hour, the mixture was extracted thoroughly with pentane. Evaporation of the pentane extracts gave an oil, which was flash chromatographed on silica using hexane. Fractions with Rf of about 0.52 on evaporation gave the title silylfuran as a yellow oil.

Workup

  1. extractionthe mixture was extracted thoroughly with pentane
  2. customEvaporation of the pentane extracts
  3. customgave an oil, which
  4. customchromatographed on silica
  5. customFractions with Rf of about 0.52 on evaporation

Sources & evidence

ORD record
ord-e83e0ba68b2b450caa207ecec239906a
Source dataset
uspto-grants-1991_05
Patent number
US05013850

Reaction notes

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