1-Bromo-2-Chloroethane → 1-(5-Bromopyridin-3-yl)cyclopropane-1-carbonitrile

HRID 2036829Notes

Reaction equation

HRID 2036829 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([CH2:10][C:11]#[N:12])[CH:7]=[N:8][CH:9]=1.Br[CH2:14][CH2:15]Cl>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[Br:3][C:4]1[CH:5]=[C:6]([C:10]2([C:11]#[N:12])[CH2:15][CH2:14]2)[CH:7]=[N:8][CH:9]=1

Participants

6

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 14798Sodium HydroxideHCID 150054172-(5-Bromopyridin-3-yl)acetonitrile

Product 1

HCID 670560001-(5-Bromopyridin-3-yl)cyclopropane-1-carbonitrileYield 59%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 7 mL NaOH (50/50 w/w in H2O) was charged with 2-(5-bromopyridin-3-yl)acetonitrile (from example 199: 0.36 g, 1.9 mmol). 1-Bromo-2-chloroethane (0.29 g, 2.01 mmol) was added followed by a catalytic amount of benzyl triethylammonium chloride (5 mg). The reaction mixture was stirred for 20 h at 60° C. and then poured into water. The resulting solution was extracted into ethyl acetate. The combined organic extracts were washed successively with water and brine, dried over Na2SO4 filtered and then concentrated to yield 1-(5-bromopyridin-3-yl)cyclopropanecarbonitrile (0.25 g, 41%), which was used without further purification. 1H NMR (400 MHz, CDCL3) δ (ppm): 8.49 (d, 1H, J=2 Hz); 7.78 (d, 1H, J=4 Hz); 3.94 (q, 2H, J=7.6 Hz); 1.69 (d, 3H, J=7.6 Hz). LCMS Method Y: retention time 1.54 min; [M+1]=212.6.

Workup

  1. extractionThe resulting solution was extracted into ethyl acetate
  2. washThe combined organic extracts were washed successively with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7ed723724249498394e650dfa574ba7c
Source dataset
uspto-grants-2013_11
Patent number
US08575184B2

Reaction notes

Loading…