Benzyl Bromide → 2-(Benzyloxy)benzonitrile

HRID 1297329Notes

Reaction equation

HRID 1297329 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([N+]([O-])=O)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[CH2:19]([O:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 2861482-Hydroxy-4-nitrobenzonitrile

Product 1

HCID 20640242-(Benzyloxy)benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Hydroxy-4-nitro-benzonitrile (11.2 g, 68 mmole) was dissolved in DMF (200 ml). Potassium carbonate (11 g, 80 mmole) and benzyl bromide (9 ml, 75 mmole) were added. The reaction was stirred at room temperature overnight. The DMF was removed in vacuo and the residue taken up in ethyl acetate and water. The organic layer was separated, washed with 1 N NaOH, then with water, and dried over sodium sulfate. The crude product (5 g) was dissolved in ethyl acetate (75 ml) and added to a flask containing 5% Pt/C (500 mg). The reaction was placed under a hydrogen atmosphere (balloon) and stirred vigorously for several hours until the reaction was done (TLC). The catalyst was filtered off and the solvent removed. The product was purified by flash chromatography to yield 4.12 g of 4-amino, 2-benzyloxybenzonitrile.

Workup

  1. customThe DMF was removed in vacuo
  2. customThe organic layer was separated
  3. washwashed with 1 N NaOH
  4. dry with materialwith water, and dried over sodium sulfate
  5. dissolutionThe crude product (5 g) was dissolved in ethyl acetate (75 ml)
  6. additionadded to a flask
  7. additioncontaining 5% Pt/C (500 mg)
  8. stirringstirred vigorously for several hours until the reaction
  9. filtrationThe catalyst was filtered off
  10. customthe solvent removed
  11. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-3bddc2c9e02c413ebad69985449eac7a
Source dataset
uspto-grants-2007_07
Patent number
US07250447B2

Reaction notes

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