3-(Bromomethyl)-5-methylbenzonitrile → Phthalimide

HRID 1956703Notes

Reaction equation

HRID 1956703 reaction equation
C(C1C=C(C=C(C)C=1)CBr)#N.[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)C=O.C(Cl)(Cl)Cl.O>[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

Participants

6

Reactant 2

HCID 145678603-(Bromomethyl)-5-methylbenzonitrileHCID 24194345Phthalimide potassium salt

Product 1

HCID 6809PhthalimideYield 107.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-cyano-5-methylbenzyl bromide from Example 7, Step 1 (15.79 g, 75.16 mmol) and potassium phthalimide (15.31 g, 82.68 mmol) in N,N-dimethylformamide (150 mL) was vigorously stirred for 4 hours. The reaction mixture was freed of solvent and the residue was dissolved in chloroform (200 mL)/water (400 mL). The chloroform fraction was separated and the aqueous phase was extracted with chloroform (2×75 mL). The combined chloroform fractions were washed with water, with brine and dried (anhydrous Na2SO4). Removal of solvent gave 20.2 g of crude product which was recrystallized from acetonitrile to yield 13.12 g (63%) of white phthalimide: mp 180°-184° C.; 1H NMR (DMSO-d6) δ7.87 (br m, 4H), 7.60 (s, br, 1H), 7.56 (s, br, 1H), 7.47 (s, br, 1H) 4.78 (s, 2H), 2.32 (s, 3H) ppm. IR (KBr): 2240, 1770, 1720 cm-1 ; MS (m/z) 276 (M+).

Workup

  1. customThe chloroform fraction was separated
  2. extractionthe aqueous phase was extracted with chloroform (2×75 mL)
  3. washThe combined chloroform fractions were washed with water, with brine
  4. dry with materialdried (anhydrous Na2SO4)
  5. customRemoval of solvent
  6. customgave 20.2 g of crude product which
  7. customwas recrystallized from acetonitrile

Sources & evidence

ORD record
ord-20b1138b6f1c4f46bbf4f75d9e524bce
Source dataset
uspto-grants-1998_07
Patent number
US05780505

Reaction notes

Loading…