Toluene → 5-(4-Ethoxyphenyl)-2-fluorobenzaldehyde

HRID 413586Notes

Reaction equation

HRID 413586 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH2:11]([O:13][C:14]1[CH:19]=[CH:18][C:17](OB(O)O)=[CH:16][CH:15]=1)[CH3:12].C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>COCCOC>[CH2:11]([O:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]2[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=2)[CH:7]=[O:8])=[CH:16][CH:15]=1)[CH3:12]

Participants

6

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 7363275-Bromo-2-fluorobenzaldehydeHCID 185333934-Ethoxyphenylboric acid

Product 1

HCID 185333825-(4-Ethoxyphenyl)-2-fluorobenzaldehydeYield 76%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Procedure

Under an argon atmosphere, tetrakistriphenylphosphine palladium (69 mg) was added to 5 ml of 1,2-dimethoxyethane. A mixture resulting from dissolving 5-bromo-2-fluorobenzaldehyde (406 mg) in 5 ml of 1,2-dimethoxyethane was added. A mixture resulting from dissolving 4-ethoxyphenylboric acid (398 mg) in 1.5 ml of 1,2-dimethoxyethane was added. Two milliliter of 2M sodium carbonate solution was added. Stirring was conducted for one hour and ten minutes under reflux. After cooling to room temperature, 20 ml of toluene was added and was washed with 10 ml of water twice, 10 ml of a 2N sodium hydroxide solution twice and 10 ml of water twice. After drying with anhydrous sodium sulfate, the mixture was concentrated. The concentrated matter was purified by silica gel chromatography (hexane/ethyl acetate=4/1). The resulting effective fractions were concentrated to yield 5-(4-ethoxyphenyl)-2-fluorobenzaldehyde (369 mg, Yield 76%).

Workup

  1. customA mixture resulting
  2. additionwas added
  3. customA mixture resulting
  4. additionwas added
  5. temperatureunder reflux
  6. washwas washed with 10 ml of water twice
  7. dry with materialAfter drying with anhydrous sodium sulfate
  8. concentrationthe mixture was concentrated
  9. customThe concentrated matter was purified by silica gel chromatography (hexane/ethyl acetate=4/1)
  10. concentrationThe resulting effective fractions were concentrated

Sources & evidence

ORD record
ord-f576b0cafd1446609f005be81cd75e7f
Source dataset
uspto-grants-2003_05
Patent number
US06566535B1

Reaction notes

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