Phthalimide → HCID 69113020, compound

HRID 2221138Notes

Reaction equation

HRID 2221138 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]1(=[O:30])[NH:24][C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12.[Br:31][C:32]1[C:40]2[O:39][C:38]([CH2:41]O)=[CH:37][C:36]=2[CH:35]=[C:34]([Cl:43])[CH:33]=1>C1(C)C=CC=CC=1.O>[Br:31][C:32]1[C:40]2[O:39][C:38]([CH2:41][N:24]3[C:20](=[O:30])[C:21]4[C:22](=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:23]3=[O:25])=[CH:37][C:36]=2[CH:35]=[C:34]([Cl:43])[CH:33]=1

Participants

6

Reactant 3

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 65439175HCID 65439175, compound

Product 1

HCID 69113020HCID 69113020, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of triphenylphoshine (1.44 g, 5.48 mmol) in toluene (50 mL) cooled to 0° C. was added the diisopropylazadicarboxylate (1.11 g, 5.48 mmol) followed by the phthalimide (0.81 g, 5.48 mmol) and the reaction mixture allowed to stir for 10 min. The (7-bromo-5-chloro-1-benzofuran-2-yl)methanol (1.37 g, 5.22 mmol) was then added and the reaction was allowed to stir at 0° C. an additional 1 h. The reaction mixture was then quenched with water (1 mL) and the solvent was removed in vacuo to provide a crude solid. The solid was suspended in water (100 mL) and the aqueous layer was extracted with ethyl acetate (3×100 mL), the combined organic extracts were washed with saturated aqueous sodium chloride (50 mL), dried (magnesium sulfate), and the solvent removed in vacuo to provide a crude residue. Purification by flash column chromatography (silica, ethyl acetate:hexanes 1:5) provided 1.73 g (85%) of 2-[(7-bromo-5-chloro-1-benzofuran-2-yl)methyl]-1H-isoindole-1,3(2H)-dione as a white solid. mp 194-198° C.; HRMS-ESI (m/z). [M+H]+ calcd for C17H9BrClNO3, 388.94545; found, 389.9553.

Workup

  1. additionwas added the diisopropylazadicarboxylate (1.11 g, 5.48 mmol)
  2. stirringto stir at 0° C. an additional 1 h
  3. customThe reaction mixture was then quenched with water (1 mL)
  4. customthe solvent was removed in vacuo
  5. customto provide a crude solid
  6. extractionthe aqueous layer was extracted with ethyl acetate (3×100 mL)
  7. washthe combined organic extracts were washed with saturated aqueous sodium chloride (50 mL)
  8. dry with materialdried (magnesium sulfate)
  9. customthe solvent removed in vacuo
  10. customto provide a crude residue
  11. customPurification by flash column chromatography (silica, ethyl acetate:hexanes 1:5)

Sources & evidence

ORD record
ord-d17c859b7d1a4acbae599db8c27729c9
Source dataset
uspto-grants-2008_05
Patent number
US07368477B2

Reaction notes

Loading…