Potassium Carbonate → 5-(4-Fluoro-benzyloxy)-isoindole-1,3-dione

HRID 431581Notes

Reaction equation

HRID 431581 reaction equation
[OH: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=[O:12].C(=O)([O-])[O-].[K+].[K+].[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1>C(O)C>[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][O:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[C:7](=[O:11])[NH:6][C:5]3=[O:12])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 105589505-Hydroxyisoindoline-1,3-dione

Product 1

HCID 223970815-(4-Fluoro-benzyloxy)-isoindole-1,3-dioneYield 46.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-hydroxy-isoindole-1,3-dione (200 mg, 1.0 mmol), potassium carbonate (178 mg, 1.05 mmol), 4-fluorobenzylbromide (204 mg, 1.05 mmol) in ethanol (5 mL) was heated at 80° C. overnight. After cooling to room temperature, the reaction mixture was filtered and evaporated. The residue was purified by chromatography (SiO2, heptane-CH2Cl2 2:3 then CH2Cl2— 2N NH3—MeOH 99:1: to 95:5) to afford the title compound (127 mg, 38%) as an off-white solid. MS: m/e=271.1 (M+).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe reaction mixture was filtered
  3. customevaporated
  4. customThe residue was purified by chromatography (SiO2, heptane-CH2Cl2 2:3

Sources & evidence

ORD record
ord-2cd8f67aa11b4c348e2d3a682edf4121
Source dataset
uspto-grants-2003_12
Patent number
US06660736B2

Reaction notes

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