5-Bromo-2-(4-methoxybenzyl)-3,3-dimethylisoindolin-1-one → 5-Bromo-3,3-dimethyl-isoindolin-1-one

HRID 605983Notes

Reaction equation

HRID 605983 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6](CC1C=CC(OC)=CC=1)[C:5]2([CH3:22])[CH3:21]>C(#N)C.O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[NH:6][C:5]2([CH3:22])[CH3:21]

Participants

5

Reactant 1

HCID 575899515-Bromo-2-(4-methoxybenzyl)-3,3-dimethylisoindolin-1-one

Product 1

HCID 575899965-Bromo-3,3-dimethyl-isoindolin-1-oneYield 86%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-bromo-2-(4-methoxybenzyl)-3,3-dimethyl-2,3-dihydroisoindol-1-one (640 mg, 1.78 mmol) and ceric ammonium nitrate (2.91 g, 5.33 mmol) in acetonitrile (11 mL) and water (5 mL) is stirred at 0° C. for 45 min. The solution is diluted with ethyl acetate (100 mL) and washed with brine (40 mL). The organic solvents are dried over MgSO4 and evaporated under reduced pressure. The residue is purified by silica chromatography, eluting with 10% to 50% ethyl acetate in petroleum ether to afford the title compound (367 mg, 1.53 mmol).

Workup

  1. washwashed with brine (40 mL)
  2. dry with materialThe organic solvents are dried over MgSO4
  3. customevaporated under reduced pressure
  4. customThe residue is purified by silica chromatography
  5. washeluting with 10% to 50% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-b9f7f6bffa3f4d24a70fc5ec56eada44
Source dataset
uspto-grants-2011_03
Patent number
US07915256B2

Reaction notes

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