Furfural → 2-(2,2-Dibromovinyl)furan

HRID 1654775Notes

Reaction equation

HRID 1654775 reaction equation
[C:1]([Br:5])(Br)(Br)[Br:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:25]1[CH:29]=[CH:28][CH:27]=[C:26]1[CH:30]=O>C(Cl)Cl>[Br:2][C:1]([Br:5])=[CH:30][C:26]1[O:25][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 7362FurfuralHCID 11205Carbon tetrabromideHCID 11776Triphenylphosphine

Product 1

HCID 108579432-(2,2-Dibromovinyl)furan

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

Mix carbon tetrabromide (49.8 g, 150 mmol) and methylene chloride (75 mL) and cool to 0° C. Add, by dropwise addition, a solution of triphenylphosphine (78.6 g, 300 mmol) in methylene chloride (75 mL). Stir at 0° C. for 30 minutes. Add, by dropwise addition, a solution of 2-furancarboxaldehyde (7.57 g , 78.8 mmol) in methylene chloride (75 mL). Remove the cooling bath and stir at room temperature until the reaction is complete. Pour onto ethyl ether and water, separate the organic layer and dry (MgSO4). Filter and evaporate the solvent in vacuo. Purify by silica gel chromatography to yield the title compound.

Workup

  1. additionAdd, by dropwise addition
  2. additionAdd, by dropwise addition
  3. customRemove the cooling bath
  4. stirringstir at room temperature until the reaction
  5. additionPour onto ethyl ether and water
  6. customseparate the organic layer
  7. dry with materialdry (MgSO4)
  8. filtrationFilter
  9. customevaporate the solvent in vacuo
  10. customPurify by silica gel chromatography

Sources & evidence

ORD record
ord-735ec900ac9d4baf974b32861eec7afb
Source dataset
uspto-grants-1995_04
Patent number
US05409942

Reaction notes

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