Water → HCID 11021491, compound

HRID 1250089Notes

Reaction equation

HRID 1250089 reaction equation
C(=O)(O)[O-].[Na+].[CH2:6]([O:8][C:9](=[O:19])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[C:11]=1Br)[CH3:7].[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:6]([O:8][C:9](=[O:19])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[C:11]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:7]

Participants

7

Reactant 4

HCID 962WaterHCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 46311271HCID 46311271, compound

Product 1

HCID 11021491HCID 11021491, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

2M Aqueous sodium bicarbonate (10 mL) was added to a suspension of 2-bromo-3-methoxybenzoic acid ethyl ester (2.06 g, 7.7 mmol), benzeneboronic acid (1.11 g), and tetrakis(triphenylphosphine)palladium(0) (0.30 g) in toluene (35 mL) under a nitrogen atmosphere. The mixture was stirred at 80° C. for 2 hours, poured into water, and extracted with diethyl ether. The organic layer was evaporated, and the residue was chromatographed, eluting with hexane/acetone (3:1) to give a semisolid oil. Recrystallization from diethyl ether/hexane gave 3-methoxy-2-phenylbenzoic acid ethyl ester as colorless crystals (0.69 g, 34%).

Workup

  1. extractionextracted with diethyl ether
  2. customThe organic layer was evaporated
  3. customthe residue was chromatographed
  4. washeluting with hexane/acetone (3:1)
  5. customto give a semisolid oil
  6. customRecrystallization from diethyl ether/hexane

Sources & evidence

ORD record
ord-26d9ad89d7e04bca9bdadc126c462f9a
Source dataset
uspto-grants-2002_01
Patent number
US06335459B1

Reaction notes

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