Dimethylformamide → 4-(3,4-dimethoxy-2-(methoxymethoxy)phenyl)isobenzofuran-1(3H)-one

HRID 2171013Notes

Reaction equation

HRID 2171013 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:14]OC)=[C:5](B(O)O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:17](=[O:20])([O-])[O-].[Cs+].[Cs+].BrC1[CH:32]=[CH:31][CH:30]=[C:29]2[C:25]=1[CH2:26][O:27][C:28]2=[O:33].CN(C)[CH:36]=[O:37]>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>[CH3:10][O:9][C:8]1[C:3]([O:2][CH2:1][O:20][CH3:17])=[C:4]([C:14]2[CH:32]=[CH:31][CH:30]=[C:29]3[C:25]=2[CH2:26][O:27][C:28]3=[O:33])[CH:5]=[CH:6][C:7]=1[O:37][CH3:36]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 115937154-Bromo-2-benzofuran-1[3H]-oneHCID 67462911[3,4-Dimethoxy-2-(methoxymethyl)phenyl]boronic acid2×

Product 1

HCID 674651214-(3,4-dimethoxy-2-(methoxymethoxy)phenyl)isobenzofuran-1(3H)-one

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

To a stirring solution of 3,4-dimethoxy-2-(methoxymethyl)phenylboronic acid (compound 301)(2.3 g, 10.79 mmol) in dimethylformamide (25 mL) under nitrogen atmosphere, were added cesium carbonate (10.52 g, 32.31 mmol), tetrakis(triphenylphosphine)palladium(0) (623 mg, 0.539 mmol) and 4-bromoisobenzofuran-1(3H)-one (5.2 g, 21.5 mmol) and the resultant reaction mixture was heated to 80° C. for 3 h. The reaction mixture was filtered off and the filtrate was extracted with ethyl acetate (3×). The combined ethyl acetate layer was washed with brine and dried over anhydrous sodium sulphate and concentrated under reduced pressure. Purification by column chromatography (silica gel, 0-30% ethyl acetate in pet ether) afforded 4-(3,4-dimethoxy-2-methoxymethoxy-phenyl)-3H-isobenzofuran-1-one as a solid.

Workup

  1. customthe resultant reaction mixture
  2. filtrationThe reaction mixture was filtered off
  3. extractionthe filtrate was extracted with ethyl acetate (3×)
  4. washThe combined ethyl acetate layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customPurification by column chromatography (silica gel, 0-30% ethyl acetate in pet ether)

Sources & evidence

ORD record
ord-195b24bb29ba47a3bff608304d6951fe
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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