Phenylpyruvic acid → HCID 12918242, compound

HRID 1376831Notes

Reaction equation

HRID 1376831 reaction equation
[C:1]1([CH2:7][C:8](=[O:12])[C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:13]Br>C(O)(=O)C>[Br:13][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8](=[O:12])[C:9]([OH:11])=[O:10]

Participants

4

Reactant 2

HCID 997Phenylpyruvic acidHCID 24408Bromine

Product 1

HCID 12918242HCID 12918242, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

12.31 g of phenyl-pyruvic acid and 50 ml of acetic acid were mixed together and then a solution of 12.34 g of bromine in 4 ml of acetic acid was added drop by drop over 1 hour. After the introduction was finished, stirring was continued for 15 minutes, followed by concentration to dryness under reduced pressure. The residue was taken up in 40 ml of dichloroethane and concentrated to dryness under reduced pressure, 30 ml of dichloroethane were added, and crystallization was allowed for 2 hours at 20° C. to obtain 12.6 g of 3-bromo-3-phenyl-pyruvic acid melting at 110° C.

Workup

  1. concentrationfollowed by concentration to dryness under reduced pressure
  2. concentrationconcentrated to dryness under reduced pressure, 30 ml of dichloroethane
  3. additionwere added
  4. customcrystallization
  5. waitwas allowed for 2 hours at 20° C.

Sources & evidence

ORD record
ord-10c4840246bd455bb6b8b9cb1ed68cc5
Source dataset
uspto-grants-1997_09
Patent number
US05663164

Reaction notes

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