2,4-Dimethoxybenzeneboronic acid → 3-(2,4-Dimethoxyphenyl)-7-methoxy-4H-1-benzopyran-4-one

HRID 1357061Notes

Reaction equation

HRID 1357061 reaction equation
Br[C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][C:7]([O:13][CH3:14])=[CH:8][CH:9]=2)[O:4][CH:3]=1.[CH3:15][O:16][C:17]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:18]=1B(O)O>C1(C)C=CC=CC=1.CCO.C([O-])([O-])=O.[Na+].[Na+]>[CH3:15][O:16][C:17]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:18]=1[C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][C:7]([O:13][CH3:14])=[CH:8][CH:9]=2)[O:4][CH:3]=1

Participants

5

Reactant 2

HCID 27343412,4-Dimethoxybenzeneboronic acidHCID 185054523-Bromo-7-methoxy-4H-1-benzopyran-4-one

Product 1

HCID 140183653-(2,4-Dimethoxyphenyl)-7-methoxy-4H-1-benzopyran-4-one

Reagents, catalysts & solvents 2

HCID 10340Sodium CarbonateSolventHCID 21863594Toluene ethanolSolvent

Procedure

A solution of 13 (4.0 g, 15.8 mmol) and 2,4-dimethoxy benzeneboronic acid (3.4 g, 19.0 mmol) and Pd(Ph3)4 (0.79 g) in toluene/EtOH (50 mL/5 mL) and 2M Na2CO3 aq. (30 mL) was heated to reflux. After 5 h, the reaction was cooled and the organic layer dried over MgSO4, concentrated and chromatographed on silica gel (EtOAc/hexanes 3:7 to EtOAc/hexanes 1:1) to yield 14 as a solid which was triturated with MeOH to give a tan solid.

Workup

  1. temperaturethe reaction was cooled
  2. dry with materialthe organic layer dried over MgSO4
  3. concentrationconcentrated
  4. customchromatographed on silica gel (EtOAc/hexanes 3:7 to EtOAc/hexanes 1:1)

Sources & evidence

ORD record
ord-ac411d9ec60f4ec2ad0f3fb258c2679b
Source dataset
uspto-grants-2003_07
Patent number
US06589980B2

Reaction notes

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