p-Xylyl bromide → 5-Methoxy-2-(4-methylbenzyl)-2,3-dihydroisoindol-1-one

HRID 2427534Notes

Reaction equation

HRID 2427534 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH2:6]2.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)[CH2:6]2

Participants

5

Reactant 3

HCID 7721p-Xylyl bromideHCID 10796Cesium carbonateHCID 220647195-methoxy-2,3-dihydro-1H-isoindol-1-one

Product 1

HCID 579497165-Methoxy-2-(4-methylbenzyl)-2,3-dihydroisoindol-1-oneYield 22.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

5-Methoxy-2,3-dihydroisoindol-1-one (40 mg, 0.25 mmol), Cs2CO3 (239 mg, 0.74 mmol), 1-bromomethyl-4-methylbenzene (68 mg, 0.37 mmol) in acetonitrile (4 mL) was allowed to stir at room temperature for 18 hours and at 70° C. for 4 hours. The reaction was partitioned between ethyl acetate and water and the organic layer was washed with brine and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure and the product was purified by column chromatography (30% EtOAc/Hexanes) to afford a white solid (15 mg). 1H NMR (300 MHz, CDCl3): δ 7.81 (d, 1H), 7.18 (q, 4H), 7.00 (dd, 1H), 6.87 (s, 1H), 4.75 (s, 2H), 4.21 (s, 2H), 3.87 (s, 3H), 2.34 (S, 3H).

Workup

  1. customThe reaction was partitioned between ethyl acetate and water
  2. washthe organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. customThe solvent was removed under reduced pressure
  5. customthe product was purified by column chromatography (30% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-ad2978ed7ada4b119a3dda1b86a02824
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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