Isopropanol → 2,3-Dimethoxy-5-phenylbenzaldehyde

HRID 218253Notes

Reaction equation

HRID 218253 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:11]1[CH:12]=[C:13]([O:21][CH3:22])[C:14]([O:19][CH3:20])=[C:15]([CH:18]=1)[CH:16]=[O:17].C(=O)([O-])[O-].[Na+].[Na+].C(O)(C)C>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.O>[CH3:20][O:19][C:14]1[C:13]([O:21][CH3:22])=[CH:12][C:11]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:18][C:15]=1[CH:16]=[O:17]

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 3224055-Bromo-2,3-dimethoxybenzaldehyde

Product 1

HCID 820388002,3-Dimethoxy-5-phenylbenzaldehyde

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent

Procedure

A stirred mixture of benzeneboronic acid (0.610 g; 5 mmol), 5-bromo-2,3-dimethoxybenzaldehyde (1.00 g; 4.1 mmol), bis(triphenylphosphine)palladium (II) chloride (0.050 g; 0.071 mmol), sodium carbonate (0.848 g; 8 mmol), isopropanol (40 mL) and water (4.0 mL) was bubbled with nitrogen for fifteen minutes then heated under reflux overnight. The mixture was evaporated, the residue stirred with water and dichloromethane and the organic layer dried and evaporated. The residue was taken up in boiling cyclohexane (40 mL twice) and filtered hot. The solution was chromatographed on silica using cyclohexane to elute triphenylphosphine and 10% ethyl acetate—90% cyclohexane to elute product 21 (0.87 g) as a white crystalline solid:

Workup

  1. customwas bubbled with nitrogen for fifteen minutes
  2. temperaturethen heated
  3. temperatureunder reflux overnight
  4. customThe mixture was evaporated
  5. customthe organic layer dried
  6. customevaporated
  7. filtrationfiltered hot
  8. customThe solution was chromatographed on silica
  9. washto elute triphenylphosphine and 10% ethyl acetate—90% cyclohexane
  10. washto elute product 21 (0.87 g) as a white crystalline solid

Sources & evidence

ORD record
ord-b0114109a7854a76973d1ebb0424ad04
Source dataset
uspto-grants-2012_06
Patent number
US08198302B2

Reaction notes

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