Ammonium Hydroxide → 6-Fluoro-2,3-dihydro-7-iodo-1H-isoindol-1-one

HRID 2427737Notes

Reaction equation

HRID 2427737 reaction equation
C[O:2][C:3](=O)[C:4]1[C:9]([I:10])=[C:8]([F:11])[CH:7]=[CH:6][C:5]=1[CH2:12]Br.[OH-].[NH4+:16]>C1COCC1>[F:11][C:8]1[C:9]([I:10])=[C:4]2[C:5]([CH2:12][NH:16][C:3]2=[O:2])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 67250389HCID 67250389, compound

Product 1

HCID 672519166-Fluoro-2,3-dihydro-7-iodo-1H-isoindol-1-oneYield 25.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 2-bromomethyl-5-fluoro-6-iodo-benzoic acid methyl ester (0.373 g, 1.0 mmol), in THF (4 mL) was treated with 30% aq. Ammonium hydroxide (0.256 mL, 2.2 mmol) and heated with stirring at 100° C. for 2 h. After this time, the resulting mixture was concentrated. Silica gel column chromatography using 30% ethyl acetate in hexane afforded 6-fluoro-7-iodo-2,3-dihydro-isoindol-1-one (0.070 g, 25%). GC-MS: m/z 277 (M)+, 249 (M−28)+.

Workup

  1. temperatureheated
  2. concentrationAfter this time, the resulting mixture was concentrated

Sources & evidence

ORD record
ord-d91cc4bfb6094bfbb043b9ead6e2882a
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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