Phthalimide potassium salt → 3-Chloro-4-((1,3-dioxoisoindolin-2-yl)methyl)benzaldehyde

HRID 1503716Notes

Reaction equation

HRID 1503716 reaction equation
Br[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][C:4]=1[Cl:11].[C:12]1(=[O:22])[NH:16][C:15](=[O:17])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12.[K]>CN(C=O)C.O>[Cl:11][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:3]=1[CH2:2][N:16]1[C:12](=[O:22])[C:13]2[C:14](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:15]1=[O:17])[CH:7]=[O:8]

Participants

5

Reactant 2

HCID 24194345Phthalimide potassium saltHCID 866751774-(Bromomethyl)-3-chlorobenzaldehyde

Product 1

HCID 866751783-Chloro-4-((1,3-dioxoisoindolin-2-yl)methyl)benzaldehydeYield 66.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 4-(bromomethyl)-3-chlorobenzaldehyde (3.8 g, 14 mmol) in DMF (40 mL) was added potassium pthalimide (3.54 g, 19.14 mmol), and the mixture was heated at 60° C. for 6 h. The reaction mixture was cooled to ambient temperature and diluted with H2O (100 mL). The solid obtained was separated by filtration and dried under vacuum to afford the title compound as a white solid (2.8 g, 60%): mp 123-126° C.; 1H NMR (400 MHz, CDCl3) δ 9.95 (s, 1H), 8.21 (s, 1H), 7.91 (m, 3H), 7.80 (m, 2H), 7.20 (m, 1H), 5.05 (s, 2H); ESIMS m/z 298.03 ([M−H]−).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customThe solid obtained
  3. customwas separated by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-d40a8525c51f40e3a97c8e25224416e6
Source dataset
uspto-grants-2015_12
Patent number
US09212164B2

Reaction notes

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