Cesium carbonate → 5-(3-Hydroxy-2,4-dimethoxy-phenyl)-3H-isobenzofuran-1-one

HRID 2171151Notes

Reaction equation

HRID 2171151 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[C:14](=[O:18])[O:13][CH2:12]3)O1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:27]1[C:28]([O:36][CH3:37])=[C:29]([OH:35])[C:30]([O:33][CH3:34])=[CH:31][CH:32]=1>CN(C)C=O.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>[OH:35][C:29]1[C:30]([O:33][CH3:34])=[C:31]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[C:14](=[O:18])[O:13][CH2:12]3)[CH:32]=[CH:27][C:28]=1[O:36][CH3:37]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 150736683-Bromo-2,6-dimethoxyphenolHCID 580746235-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3H-2-benzofuran-1-one

Product 1

HCID 674677565-(3-Hydroxy-2,4-dimethoxy-phenyl)-3H-isobenzofuran-1-oneYield 40.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A stirring solution of 5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3H-isobenzofuran-1-one (2.23 g, 8.58 mmol) in dimethylformamide (30 mL) was purged with argon for 1 h, to this cesium carbonate (8.37 g, 25.74 mmol), Pd(PPh3)4 (495 mg, 0.429 mmol) and 3-bromo-2,6-dimethoxy-phenol (2.0 g, 8.58 mmol) were added and the resultant reaction mixture was heated to 80-90° C. for 16 h. The reaction mixture was cooled to RT, filtered through celite and the filtrate was diluted with water and extracted with ethyl acetate (3×). The combined ethyl acetate layers were washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. Purification of the residue by column chromatography (silica gel, 0-10% ethyl acetate in pet ether) afforded the title compound as a solid (1 g, 40.7%).

Workup

  1. additionwere added
  2. customthe resultant reaction mixture
  3. temperatureThe reaction mixture was cooled to RT
  4. filtrationfiltered through celite
  5. additionthe filtrate was diluted with water
  6. extractionextracted with ethyl acetate (3×)
  7. washThe combined ethyl acetate layers were washed with brine
  8. dry with materialdried over anhydrous sodium sulphate
  9. concentrationconcentrated under reduced pressure
  10. customPurification of the residue by column chromatography (silica gel, 0-10% ethyl acetate in pet ether)

Sources & evidence

ORD record
ord-caacbf7f13a14a2199c34305a81c3c33
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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