Toluene → 2-Methoxy-4-phenylbenzaldehyde

HRID 1470630Notes

Reaction equation

HRID 1470630 reaction equation
[C:1]1(C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:14][O:15][C:16]1[CH:23]=[C:22](Br)[CH:21]=[CH:20][C:17]=1[CH:18]=[O:19].C1(B(O)O)C=CC=CC=1>O>[CH3:14][O:15][C:16]1[CH:23]=[C:22]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:21]=[CH:20][C:17]=1[CH:18]=[O:19]

Participants

6

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 110530414-Bromo-2-methoxybenzaldehyde

Product 1

HCID 109658272-Methoxy-4-phenylbenzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of toluene (30 mL) and water (5 mL) was degassed with nitrogen for 30 min. A mixture of sodium carbonate (2.26 g, 6.9 mmol) was added followed by 2-methoxy-4-bromobenzaldehyde (0.5 g, 2.3 mmol), phenylboronic acid (0.337 g, 2.7 mmol) and tetrakis triphenyl phosphene palladium(0) (0.261 g, 0.022 mmol) to the above degassed water/toluene mixture. The reaction mixture was then refluxed overnight. After the reaction is completed, it was cooled to room temperature and extracted with ethyl acetate. The combined organic layers were dried over sodium sulphate and concentrated. The obtained residue was purified by column chromatography using 3% ethyl acetate in hexane to obtain the title compound.

Workup

  1. customwas degassed with nitrogen for 30 min
  2. additionwas added
  3. customabove degassed water/toluene mixture
  4. temperatureThe reaction mixture was then refluxed overnight
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined organic layers were dried over sodium sulphate
  7. concentrationconcentrated
  8. customThe obtained residue was purified by column chromatography

Sources & evidence

ORD record
ord-fc1724b8ac8840b8b84d52cff4a513cf
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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