Potassium Carbonate → 5-Bromo-7-methyl-2-(4-phenoxybenzyl)-2,3-dihydroisoindol-1-one

HRID 2427504Notes

Reaction equation

HRID 2427504 reaction equation
CO[C:3](=[O:14])[C:4]1[C:9]([CH3:10])=[CH:8][C:7]([Br:11])=[CH:6][C:5]=1[CH2:12]Br.[O:15]([C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH2:27])=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[Br:11][C:7]1[CH:6]=[C:5]2[C:4](=[C:9]([CH3:10])[CH:8]=1)[C:3](=[O:14])[N:27]([CH2:26][C:25]1[CH:28]=[CH:29][C:22]([O:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:23][CH:24]=1)[CH2:12]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2760343(4-Phenoxyphenyl)methanamineHCID 59512232HCID 59512232, compound

Product 1

HCID 116039005-Bromo-7-methyl-2-(4-phenoxybenzyl)-2,3-dihydroisoindol-1-oneYield 67.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Bromo-2-bromomethyl-6-methylbenzoic acid methyl ester (762 mg, 2.37 mmol), 4-phenoxy benzylamine (0.543 mL, 3.56 mmol) and K2CO3 (981 mg, 7.10 mmol) were stirred in toluene (10 mL) at 95° C. for 12 hours. The reaction was partitioned between ethyl acetate and water and the organic layer was washed with brine and dried over anhydrous Na2-SO4. The solvent was removed under reduced pressure and the product was purified by column chromatography (10-25% EtOAc/Hexanes) to afford a yellow oil (650 mg). 1H NMR (300 MHz, CDCl3): δ 7.35-7.38 (m, 4H), 7.32 (s, 1H), 7.26-7.29 (m, 1H), 7.15 (t, 1H), 6.99 (t, 4H), 4.74 (s, 2H), 4.23 (s, 2H), 2.75 (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 Na2-SO4
  4. customThe solvent was removed under reduced pressure
  5. customthe product was purified by column chromatography (10-25% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-18a2a1dd411a4e899d66aa56d7a303ba
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

Loading…