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

HRID 1504669Notes

Reaction equation

HRID 1504669 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-491f9e0969574a9cb282ab624e712b64
Source dataset
uspto-grants-2015_12
Patent number
US09215870B2

Reaction notes

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