Potassium Carbonate → 5-(4-Fluoro-benzyloxy)-2-(2-methoxy-ethyl)-isoindole-1,3-dione

HRID 1070687Notes

Reaction equation

HRID 1070687 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([CH2:12][CH2:13][O:14][CH3:15])[C:5]2=[O:16].C(=O)([O-])[O-].[K+].[K+].[F:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=1>CC(C)=O>[F:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][O:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[C:7](=[O:11])[N:6]([CH2:12][CH2:13][O:14][CH3:15])[C:5]3=[O:16])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 148489615-Hydroxy-2-(2-methoxy-ethyl)-isoindole-1,3-dione

Product 1

HCID 102367635-(4-Fluoro-benzyloxy)-2-(2-methoxy-ethyl)-isoindole-1,3-dioneYield 66%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5-hydroxy-2-(2-methoxy-ethyl)-isoindole-1,3-dione, from example 13a, (570 mg, 2.6 mmol), potassium carbonate (445 mg, 3.2 mmol) and 4-fluorobenzyl-bromide (526 mg, 2.8 mmol) in acetone (40 mL) was heated under reflux for 17 h. After cooling to room temperature, the mixture was filtered, evaporated and the residue was purified by crystallization from diethylether:heptane (1:2) to afford the title compound (560 mg, 66%) as a white solid. MS: m/e=330.4 (M+H+).

Workup

  1. temperatureunder reflux for 17 h
  2. filtrationthe mixture was filtered
  3. customevaporated
  4. customthe residue was purified by crystallization from diethylether:heptane (1:2)

Sources & evidence

ORD record
ord-94e15c6b9bab40108d7c52beff9e4afd
Source dataset
uspto-grants-2005_06
Patent number
US06903095B2

Reaction notes

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