Bromide ion → HCID 15578417, compound

HRID 2417960Notes

Reaction equation

HRID 2417960 reaction equation
[Br-:1].[C:2]1([C:8](=[O:20])[CH2:9][C:10](=[O:19])[CH2:11][C:12](=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)(Cl)Cl>[Br:1][C:11]1[C:10](=[O:19])[CH:9]=[C:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[O:20][C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

4

Reactant 2

HCID 259Bromide ionHCID 15578433HCID 15578433, compound

Product 1

HCID 15578417HCID 15578417, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of bromide (10.25 ml, 0.198 mol) in chloroform (50 ml) was added dropwise over 30 minutes to a stirred solution of ethyl 6-phenyl-2,4,6-trioxohexanoate (52.0 g) in chloroform (400 ml) at -10 to -20° C. The pale solution was stirred for a further 3 hours without cooling, washed with water and evaporated. The residual solid was recrystallised from ethanol-water to give ethyl 3-bromo-4-oxo-6-phenyl-4H-pyran-2-carboxylate (mp 135° C.). This ester was hydrolysed as in Example 33 to give the title product (mp 247° C. with decomposition).

Workup

  1. temperaturewithout cooling
  2. washwashed with water
  3. customevaporated
  4. customThe residual solid was recrystallised from ethanol-water

Sources & evidence

ORD record
ord-fd0c84017f964230b81a112ce1ad34bc
Source dataset
uspto-grants-1984_09
Patent number
US04471129

Reaction notes

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