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

HRID 1438273Notes

Reaction equation

HRID 1438273 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, 3H) 2.85 (q, J=7.60 Hz, 2H) 4.84 (s, 2H) 7.14-7.18 (m, 1H) 7.24-7.27 (m, 1H) 7.34 (d, J=2.07 Hz, 1H) 7.73 (dd, J=5.46, 3.01 Hz, 2H) 7.86 (dd, J=5.56, 3.11 Hz, 2H).

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-3c1ab204545e4aa8a5bc51c9ccc09950
Source dataset
uspto-grants-2009_11
Patent number
US07622605B2

Reaction notes

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