1,4-Dibromobutane → 1-(1-Naphthyl)cyclopentanecarbonitrile

HRID 2169373Notes

Reaction equation

HRID 2169373 reaction equation
[H-].[Na+].[C:3]1([CH2:13][C:14]#[N:15])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.Br[CH2:17][CH2:18][CH2:19][CH2:20]Br.C(OCC)(=O)C>CS(C)=O.CCCCCC>[C:3]1([C:13]2([C:14]#[N:15])[CH2:20][CH2:19][CH2:18][CH2:17]2)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 80561,4-DibromobutaneHCID 85961-NaphthaleneacetonitrileHCID 8857Ethyl AcetateHCID 24758Sodium hydride

Product 1

HCID 122186581-(1-Naphthyl)cyclopentanecarbonitrileYield 63.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8058HexaneSolvent

Procedure

To a suspension of sodium hydride (60% in mineral oil, 5.24 g, 131.6 mmol) in dimethyl sulfoxide (50 mL) was added dropwise a mixture of naphthalen-1-yl-acetonitrile (337) (10.0 g, 59.8 mmol) and 1,4-dibromobutane (12.91 g, 59.8 mmol) dissolved in dimethyl sulfoxide-ether (1:1; 120 mL) at 0° C. and stirred for 30 min at the same temperature and then stirred at room temperature for 4 h (silica TLC, 10% ethyl acetate in hexane, Rf=0.65). The reaction mixture was quenched with HCl [1N; 20 mL] at 0° C. Ethyl acetate (400 mL) was added and the mixture was washed with water (500 mL) and brine (2×200 ml) and dried and concentrated in vacuo to get a crude mass which was purified by CombiFlash using a gradient eluent; mixture of ethyl acetate and hexane to get pure 1-naphthalen-1-yl-cyclopentanecarbonitrile (338) (8.4 g, 63%) as a white solid.

Workup

  1. additionwas added dropwise
  2. customThe reaction mixture was quenched with HCl [1N; 20 mL] at 0° C
  3. additionEthyl acetate (400 mL) was added
  4. washthe mixture was washed with water (500 mL) and brine (2×200 ml)
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customto get a crude mass which
  8. customwas purified by CombiFlash
  9. additionmixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-cfefa627ab214694a24916612dd200f5
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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