Dimethylformamide → 5-(3,4-dimethoxy-2-(methoxymethoxy)phenyl)isobenzofuran-1(3H)-one

HRID 2171015Notes

Reaction equation

HRID 2171015 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:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[C:29](=[O:33])[O:28][CH2:27]2.CN(C)[CH:36]=[O:37]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=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:25]=[C:26]3[C:30](=[CH:31][CH:32]=2)[C:29](=[O:33])[O:28][CH2:27]3)[CH:5]=[CH:6][C:7]=1[O:37][CH3:36]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 6031445-BromophthalideHCID 67462911[3,4-Dimethoxy-2-(methoxymethyl)phenyl]boronic acid2×

Product 1

HCID 674667495-(3,4-dimethoxy-2-(methoxymethoxy)phenyl)isobenzofuran-1(3H)-one

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Conditions

Temperature
70 °C

Procedure

To a stirring solution of 3,4-dimethoxy-2-(methoxymethyl)phenylboronic acid (Compound 301) (3.5 g, 16.58 mmol) in dimethylformamide (50 mL) under nitrogen atmosphere, were added cesium carbonate (16.17 g, 49.75 mmol), tetrakis(triphenylphosphine) palladium(0) (957 mg, 0.828 mmol) and 5-bromoisobenzofuran-1(3H)-one (8.02 g, 33.14 mmol) and the resultant reaction mixture was heated to 70° 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, dried over anhydrous sodium sulphate and concentrated under reduced pressure. Purification by column chromatography (silica gel, 0-30% ethyl acetate in pet ether) afforded 5-(3,4-dimethoxy-2-(methoxymethoxy)phenyl)isobenzofuran-1(3H)-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-144ab6755aa14343be2d601c76d81b55
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

Loading…