Bromine → HCID 15578417, compound

HRID 544173Notes

Reaction equation

HRID 544173 reaction equation
[Br:1]Br.[C:3]1([C:9](=[O:21])[CH2:10][C:11](=[O:20])[CH2:12][C:13](=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(Cl)(Cl)Cl>[Br:1][C:12]1[C:11](=[O:20])[CH:10]=[C:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[O:21][C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

4

Reactant 2

HCID 24408BromineHCID 15578433HCID 15578433, compound

Product 1

HCID 15578417HCID 15578417, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of bromine (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-10cb5abea0ac4bb487ab04de7f4dcf33
Source dataset
uspto-grants-1984_05
Patent number
US04448787

Reaction notes

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