Furfural → 2-(2,2-Dibromovinyl)furan

HRID 1263946Notes

Reaction equation

HRID 1263946 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(N(CC)CC)C>ClCCl.CCOCC>[Br:2][C:1]([Br:5])=[CH:30][C:26]1[O:25][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 50%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

Carbon tetrabromide (20 mmole) was dissolved in anhydrous diohloromethane (200 mL), and kept at 20° C. under argon atmosphere. Triphenylphosphine (20 mmole) in dichloromethane (200 mL) was added dropwise. After 15 minutes of stirring, the reaction flask was kept at −60° C., followed by the addition of furaldehyde (10 mmole) and triethylamine (10 mmole) in dichloromethane (100 mL). The reaction mixture was brought to room temperature, and two volumes of ether were added. The precipitate was filtered, and the filtrate was dried. The crude material was purified by Si gel column chromatography (>50% yield).

Workup

  1. customkept at 20° C. under argon atmosphere
  2. customwas kept at −60° C.
  3. customwas brought to room temperature
  4. filtrationThe precipitate was filtered
  5. customthe filtrate was dried
  6. customThe crude material was purified by Si gel column chromatography (>50% yield)

Sources & evidence

ORD record
ord-e21555876b734897a92de73aaa6753d8
Source dataset
uspto-grants-2003_04
Patent number
US06541506B1

Reaction notes

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