Benzyl Bromide → 2-(2-Naphthalenyl)-3-phenylpropionitrile

HRID 330263

Reaction equation

HRID 330263 reaction equation
[H-].[Na+].[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[CH2:13][C:14]#[N:15].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>COCCOC>[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[CH:13]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:14]#[N:15]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 820082-Naphthylacetonitrile

Product 1

HCID 149606362-(2-Naphthalenyl)-3-phenylpropionitrileYield 40%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a refluxing solution of NaH (3.00 g, 75 mmol, 60% dispersion) in DME (150 mL) was added a solution of 2-naphthaleneacetonitrile (12.5 g, 75 mmol) and benzyl bromide (12.8 g, 75 mmol) in DME (75 mL) dropwise over 50 minutes. The resulting solution was kept at reflux for 3 hours and then cooled to room temperature. The volatiles were removed in vacuo and the residue was partitioned between Et2O (100 mL) and H2O (100 mL). The aqueous phase was washed with Et2O (1×150 mL), the organics were dried (MgSO4) and concentrated in vacuo. This residue was purified by preparative HPLC (SiO2 : gradient hexane/EtOAc) to give the title compound as a white solid (7.71 g, 40%).

Workup

  1. temperatureat reflux for 3 hours
  2. customThe volatiles were removed in vacuo
  3. customthe residue was partitioned between Et2O (100 mL) and H2O (100 mL)
  4. washThe aqueous phase was washed with Et2O (1×150 mL)
  5. dry with materialthe organics were dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThis residue was purified by preparative HPLC (SiO2 : gradient hexane/EtOAc)

Sources & evidence

ORD record
ord-d15056049a82458a98917c13f3a87301
Source dataset
uspto-grants-1990_01
Patent number
US04895861

Linked notes

Loading…