4-(Bromomethyl)benzonitrile → HCID 854235, compound

HRID 485272Notes

Reaction equation

HRID 485272 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].Br[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=1>CN(C=O)C>[C:1]1(=[O:11])[N:5]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=2)[C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12

Participants

4

Reactant 2

HCID 869964-(Bromomethyl)benzonitrileHCID 24194345Phthalimide potassium salt

Product 1

HCID 854235HCID 854235, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
90 °C

Procedure

To a suspension of 37 g (0.2 mol) of potassium phthalimide in 200 ml of DMF was added 50 ml of a solution of 19.6 g (0.1 mol) of α-bromo-p-tolunitrile in DMF at room temperature in argon atmosphere. The reaction mixture was stirred at 90° C. for 3 hours, then cooled to room temperature and poured into 400 ml of ice-water, followed by extraction with benzene-ether (1:1). The organic layer was washed with saturated aqueous solution of sodium chloride, dried over Na2SO4 and concentrated, giving 24.9 g (yield 95%) of 4-phthalimidomethylbenzonitrile.

Workup

  1. temperaturecooled to room temperature
  2. extractionfollowed by extraction with benzene-ether (1:1)
  3. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6f36f205595a42c0ad57c603dcf91ee1
Source dataset
uspto-grants-1985_08
Patent number
US04536391

Reaction notes

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