Water → 2-(3,4-Diethoxy-2-fluorobenzyl)isoindol-1,3-dione

HRID 732252Notes

Reaction equation

HRID 732252 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:5]=1[O:11][CH2:12][CH3:13])[CH3:2].O[CH2:15][N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26].S(=O)(=O)(O)O.O>COCCOC>[CH2:12]([O:11][C:5]1[C:6]([F:10])=[C:7]([CH:8]=[CH:9][C:4]=1[O:3][CH2:1][CH3:2])[CH2:15][N:16]1[C:20](=[O:21])[C:19]2[C:18](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:17]1=[O:26])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 8354N-(hydroxymethyl)phthalimideHCID 224601261,2-Diethoxy-3-fluorobenzene

Product 1

HCID 578383682-(3,4-Diethoxy-2-fluorobenzyl)isoindol-1,3-dioneYield 23%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a solution of 1,2-diethoxy-3-fluorobenzene (2.28 g, 12.4 mol) and N-(hydroxymethyl)phthalimide (2.41 g, 13.6 mol) in 1,2-dimethoxyethane (8 mL), a solution of sulfuric acid (8 mL) in 1,2-dimethoxyethane (8 mL) was added dropwise on ice, and the mixture was stirred at room temperature for twelve hours. The reaction mixture was poured into water (100 mL), and crystals were filtered. The obtained crystals were recrystallized from acetone and water, and the precipitated crystals were filtered. After the filtrate was concentrated under reduced pressure, the residue was crystallized from acetone to give 0.96 g of the title compound (yield: 23%) as white crystals.

Workup

  1. filtrationwere filtered
  2. customThe obtained crystals were recrystallized from acetone and water
  3. filtrationthe precipitated crystals were filtered
  4. concentrationAfter the filtrate was concentrated under reduced pressure
  5. customthe residue was crystallized from acetone

Sources & evidence

ORD record
ord-de0ff2b6a9f24d898d68160762ad761c
Source dataset
uspto-grants-2009_09
Patent number
US07585982B2

Reaction notes

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