Sodium Carbonate → Methyl 2-Methoxy-5-phenylbenzoate

HRID 49948Notes

Reaction equation

HRID 49948 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10](I)=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].[C:14]1(B(O)O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 11011762Methyl 5-iodo-2-methoxybenzoate

Product 1

HCID 17834364Methyl 2-Methoxy-5-phenylbenzoate

Reagents, catalysts & solvents 1

HCID 86587398Ethanol toluene waterSolvent

Procedure

1.06 g (3.64 mmol) of methyl 2-Methoxy-5-iodobenzoate, 460 mg (3.78 mmol) of phenylboronic acid, 83 mg (2 molar %) of tetrakistriphenylphosphine palladium and 1.52 g (14.4 mmol) of sodium carbonate were heated under reflux in 12 ml of toluene/ethanol/water (2/1/1) solvent mixture for 2 hours. After the filtration through Celite followed by the after treatment conducted by an ordinary method, the obtained residue was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. filtrationAfter the filtration through Celite
  2. customthe obtained residue was purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-d5ac6a06c4dc433c956f903fd447e190
Source dataset
uspto-grants-2004_03
Patent number
US06710056B2

Reaction notes

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