Water → Ethyl 2-(1,3-dioxoisoindolin-2-yl)-2-fluoroacetate

HRID 363440Notes

Reaction equation

HRID 363440 reaction equation
Br[CH:2]([F:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:9]1([C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][O:11]1)=[O:10].[K].CCOCC.O.C[N:27](C)C=O>>[O:10]=[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:11])[N:27]1[CH:2]([F:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

6

Reactant 5

HCID 962WaterHCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 2733407Acetic acid, 2-bromo-2-fluoro-, ethyl esterHCID 67006573Potassium phthalide

Product 1

HCID 13594881Ethyl 2-(1,3-dioxoisoindolin-2-yl)-2-fluoroacetate

Conditions

Temperature
80 °C

Procedure

A stirred mixture of ethyl bromofluoroacetate (1.0 g, 5.4 mmol) and potassium phthalide (1.0 g, 5.4 mmol) in dimethylformamide (10 mL) is heated at 80° C. for 3 hours. The mixture is stirred with ether (50 mL) and water (50 mL) and the organic layer then washed with water and brine (30 mL each), and dried over sodium sulfate. The solvent is removed in vacuo to give ethyl 2-(1,3-dioxoisoindolin-2-yl)-2-fluoroacetate which is further purified through chromatography.

Workup

  1. washthe organic layer then washed with water and brine (30 mL each)
  2. dry with materialdried over sodium sulfate
  3. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-adc2f0d352cc4ef2ad1036de8b178de2
Source dataset
uspto-grants-1999_02
Patent number
US05874448

Reaction notes

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