Water → 2-(4-Bromo-2-ethyl-benzyl)-isoindole-1,3-dione

HRID 2387080Notes

Reaction equation

HRID 2387080 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Br)=[C:4]([CH2:10][CH3:11])[CH:3]=1.[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].O>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:16]2[C:12](=[O:22])[C:13]3[C:14](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:15]2=[O:17])=[C:4]([CH2:10][CH3:11])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24194345Phthalimide potassium saltHCID 587640754-Bromo-1-(bromomethyl)-2-ethylbenzene

Product 1

HCID 587642872-(4-Bromo-2-ethyl-benzyl)-isoindole-1,3-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To 4-bromo-1-bromomethyl-2-ethyl-benzene (4.0 g, 14.2 mmol) in dimethylformamide (100 mL) at room temperature was added potassium phthalimide (2.9 g, 15.6 mmol), and the solution was heated at 80° C. for 5 h. The solution was cooled to room temperature and poured into water. The aqueous solution was extracted with ethyl acetate. The pooled organics were washed with saturated sodium chloride, dried (Na2SO4), filtered, and concentrated in vacuo to a yellow solid (4.0 g, 82%). 1H NMR (300 MHz, CDCl3): δ ppm 1.27 (t, J=7.54 Hz, 3 H) 2.85 (q, J=7.60 Hz, 2 H) 4.84 (s, 2 H) 7.14-7.18 (m, 1 H) 7.24-7.27 (m, 1 H) 7.34 (d, J=2.07 Hz, 1 H) 7.73 (dd, J=5.46, 3.01 Hz, 2 H) 7.86 (dd, J=5.56, 3.11 Hz, 2 H).

Workup

  1. temperatureThe solution was cooled to room temperature
  2. extractionThe aqueous solution was extracted with ethyl acetate
  3. washThe pooled organics were washed with saturated sodium chloride
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to a yellow solid (4.0 g, 82%)

Sources & evidence

ORD record
ord-bb1807c710244abfb8bacd13278b19ee
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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