Potassium Carbonate → HCID 23634683, compound

HRID 553294Notes

Reaction equation

HRID 553294 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7](Br)[CH:6]=1.[CH:13]([C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1)=[O:14].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.CO>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:6]=[C:7]([C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([CH:13]=[O:14])[CH:20]=2)[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27343563-Formylphenylboronic acidHCID 11746402Methyl 2-(3-bromophenyl)acetate

Product 1

HCID 23634683HCID 23634683, compound

Reagents, catalysts & solvents 1

HCID 21867641Toluene methanolSolvent

Procedure

A mixture of (3-bromo-phenyl)-acetic acid methyl ester (5 g), 3-formyl phenyl boronic acid (5 g) and potassium carbonate (9 g) in toluene/methanol [10:1] (33 mL) was degassed with nitrogen for 1 hour. Tetrakis(triphenylphosphine)palladium(0) (1.3 g) was washed with ethanol, under nitrogen, until golden in colour and added to the mixture. The resultant mixture was heated to reflux for 24 hours. On cooling, the reaction was diluted with iso-hexane/diethyl ether [4:1] (100 mL) and filtered through a Celite pad. The filtrate was evaporated and the residue purified on silica, eluting iso-hexane/ethyl acetate [4:1] to give the subtitle product, as an oil (3.7 g).

Workup

  1. customwas degassed with nitrogen for 1 hour
  2. washTetrakis(triphenylphosphine)palladium(0) (1.3 g) was washed with ethanol, under nitrogen
  3. additionuntil golden in colour and added to the mixture
  4. temperatureThe resultant mixture was heated
  5. temperatureto reflux for 24 hours
  6. temperatureOn cooling
  7. additionthe reaction was diluted with iso-hexane/diethyl ether [4:1] (100 mL)
  8. filtrationfiltered through a Celite pad
  9. customThe filtrate was evaporated
  10. customthe residue purified on silica
  11. washeluting iso-hexane/ethyl acetate [4:1]

Sources & evidence

ORD record
ord-c74a866e6f0144deb98ebb7e03faa527
Source dataset
uspto-grants-2011_05
Patent number
US07951954B2

Reaction notes

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