Ethanol → HCID 22049660, compound

HRID 1830836Notes

Reaction equation

HRID 1830836 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8](Br)=[CH:7][C:4]=1[CH:5]=[O:6].[F:12][C:13]([F:25])([F:24])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1OB(O)O.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[C:13]([F:25])([F:24])[F:12])=[CH:7][C:4]=1[CH:5]=[O:6]

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 906845-Bromo-2-methoxybenzaldehydeHCID 22049664HCID 22049664, compound

Product 1

HCID 22049660HCID 22049660, compoundYield 71.5%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

In 70 ml of toluene were suspended 320 mg of 2-methoxy-5-bromobenzaldehyde, 570 mg of 2-trifluoromethylphenylboric acid, 45 mg of palladium acetate and 136 mg of tri-o-tollylphosphine under nitrogen atmosphere, and then, 3.3 ml of 2M aqueous sodium carbonate solution was added to the suspension, and a small amount of ethanol was further added thereto. The obtained solution was heated up to 70° C., and stirred for 16 hours. The reaction mixture was cooled to room temperature, and the formed black precipitates were removed by filtration. The filtrate was washed with an aqueous sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The concentrated residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=10/1) and crystallized from diisopropyl ether and n-hexane to give 298 mg of 2-methoxy-5-(2-trifluoromethylphenyl)benzaldehyde.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe formed black precipitates
  3. customwere removed by filtration
  4. washThe filtrate was washed with an aqueous sodium bicarbonate solution and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe concentrated residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=10/1)
  8. customcrystallized from diisopropyl ether and n-hexane

Sources & evidence

ORD record
ord-8f5bdc8224e64218b03d96d767fdd024
Source dataset
uspto-grants-2006_06
Patent number
US07067535B2

Reaction notes

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