p-Bromoacetophenone → 1,3-Propanedione, 1,3-bis(4-bromophenyl)-

HRID 2244957Notes

Reaction equation

HRID 2244957 reaction equation
C(O[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1)C.C[O-].[Na+].[Br:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](=[O:25])[CH3:24])=[CH:19][CH:18]=1>C(OCC)C>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](=[O:25])[CH2:24][C:4]([C:5]2[CH:6]=[CH:7][C:8]([Br:11])=[CH:9][CH:10]=2)=[O:12])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7466p-BromoacetophenoneHCID 22043Ethyl 4-bromobenzoateHCID 10942334Sodium Methoxide

Product 1

HCID 1474381,3-Propanedione, 1,3-bis(4-bromophenyl)-

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A mixture of ethyl-4-bromobenzoate and sodium methoxide in dry diethyl ether was stirred under an argon atmosphere After 30 min, a solution of 4′-bromoacetophenone in dry diethyl ether was then added drop-wise under stirring. The reaction mixture was stirred for 48 h under argon at room temperature. The muddy mixture was acidified and filtered under reduced pressure. The filtrate was washed with water until pH reaches about 7. The crude product was decolourized with activated charcoal and further purified by recrystallization from ethyl acetate. The white needle crystals obtained was dried in a vacuum oven at 40° C. for 24 h. Yield: 5.40 g (28.3%). M.P.: 193.2-195.4° C. The structure was confirmed by EI-MS, 1H NMR, 13C NMR, FT-IR, UV-Vis spectroscopy, and elemental analysis.

Workup

  1. stirringunder stirring
  2. stirringThe reaction mixture was stirred for 48 h under argon at room temperature
  3. filtrationfiltered under reduced pressure
  4. washThe filtrate was washed with water until pH
  5. customfurther purified by recrystallization from ethyl acetate
  6. customThe white needle crystals obtained
  7. customwas dried in a vacuum oven at 40° C. for 24 h

Sources & evidence

ORD record
ord-05938eff83b74383af5c816ee582aaf1
Source dataset
uspto-grants-2010_03
Patent number
US07679082B2

Reaction notes

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