HCID 9815158, compound → 2(5H)-Furanone, 5-(dibromomethylene)-

HRID 2420626Notes

Reaction equation

HRID 2420626 reaction equation
BrC1=C(CCCC)C(=O)O/C/1=C\Br.C([C:18]1[C:19](=[O:26])[O:20][C:21](=[C:23]([Br:25])[Br:24])[CH:22]=1)CCC>>[Br:24][C:23]([Br:25])=[C:21]1[O:20][C:19](=[O:26])[CH:18]=[CH:22]1

Participants

3

Reactant 2

HCID 9815158HCID 9815158, compoundHCID 9839657HCID 9839657, compound

Product 1

HCID 3150692(5H)-Furanone, 5-(dibromomethylene)-

Procedure

The furanones to be used in accordance with the present invention may be obtained from natural sources or chemically synthesized. For example, (5Z)-4-bromo-5-(bromomethylene)-3-butyl-2(5H)-furanone and 3-butyl-5-(dibromomethylene)-2-(5H)-furanone may be extracted and purified from seaweed (e.g., the marine algae Delisea pulchra) as previously described (see, e.g., de Nys et al. Tetrahedron 1993; 49:11213-11220). Alternatively, (5Z)-4-bromo-5-(bromomethylene)-3-butyl-2(5H)-furanone, 3-butyl-5-(dibromomethylene)-2-(5H)-furanone, 5-(bromomethylene)-2-(5H)-furanone, 4-bromo-5-(bromomethylene)-2(5H)-furanone, and/or 5-(dibromomethylene)-2(5H)-furanone may be chemically synthesized as previously described (see, e.g.: Beechan and Sims. Tetrahedron Letters 1979; 19:1649-1652; Manny et al. Tetrahedron. 1997; 53:15813-15826; and Ren, Sims and Wood. Let. Appl. Microbiol. 2002; 34-293-299).

Workup

  1. custommay be obtained from natural sources
  2. customchemically synthesized
  3. custompurified from seaweed (e.g.
  4. customAlternatively, (5Z)-4-bromo-5-(bromomethylene)-3-butyl-2(5H)-furanone, 3-butyl-5-(dibromomethylene)-2-(5H)-furanone, 5-(bromomethylene)-2-(5H)-furanone, 4-bromo-5-(bromomethylene)-2(5H)-furanone, and/or 5-(dibromomethylene)-2(5H)-furanone may be chemically synthesized

Sources & evidence

ORD record
ord-6c796b22380d430f9aa6ebf2c8623820
Source dataset
uspto-grants-2011_06
Patent number
US07955596B2

Reaction notes

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