Furfural → 2-(2,2-Dibromovinyl)furan

HRID 1024532Notes

Reaction equation

HRID 1024532 reaction equation
[C:1]([Br:5])(Br)(Br)[Br:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:25](=O)[C:26]1[O:30][CH:29]=[CH:28][CH:27]=1.C(N(CC)CC)C>C(Cl)Cl.C(OCC)C>[Br:2][C:1]([Br:5])=[CH:25][C:26]1[O:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 7362FurfuralHCID 8471TriethylamineHCID 11205Carbon tetrabromideHCID 11776Triphenylphosphine

Product 1

HCID 108579432-(2,2-Dibromovinyl)furanYield 64.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-60 °C

Procedure

A solution of carbon tetrabromide (241.6 g, 0.73 mol) in anhydrous DCM (1000 mL) was cooled to −20° C. under nitrogen and triphenylphosphine (191.1 g, 0.73 mol) in anhydrous DCM (1000 mL) was added drop wise. After twenty minutes of stirring, the reaction was cooled to −60° C., and then a mixture of furfural (30 mL, 0.36 mol) and triethylamine (50.5 mL, 0.36 mol) in anhydrous DCM (375 mL) were added drop wise. The mixture was brought to room temperature and diethyl ether (500 mL) was added with stirring. The reaction was filtered and filtrate was concentrated in vacuo. Column chromatography (SiO2, heptanes) yielded the title compound (58.1 g, 63%) as a brown oil:

Workup

  1. additionwere added drop wise
  2. customwas brought to room temperature
  3. stirringwith stirring
  4. filtrationThe reaction was filtered
  5. concentrationfiltrate was concentrated in vacuo

Sources & evidence

ORD record
ord-5787f0b58a554108bd8ebb9048f26b4b
Source dataset
uspto-grants-2014_05
Patent number
US08722910B2

Reaction notes

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