1,2-Dibromoethane → HCID 66618800, compound

HRID 406384Notes

Reaction equation

HRID 406384 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([CH3:9])=[CH:4][C:3]=1[CH2:10][C:11]#[N:12].Br[CH2:14][CH2:15]Br.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.COC(C)(C)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([CH3:9])=[CH:4][C:3]=1[C:10]1([C:11]#[N:12])[CH2:15][CH2:14]1

Participants

6

Reactant 3

HCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 66618771HCID 66618771, compound

Product 1

HCID 66618800HCID 66618800, compoundYield 72.9%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a mixture of (2,4-dichloro-5-methylphenyl)acetonitrile (385 mg) and 1,2-dibromoethane (1.0 g) were added benzyltriethylammonium-chloride (44 mg) and a 50% solution of sodium hydroxide (0.8 ml) and the mixture was stirred overnight at room temperature. Ice-cold water and tert-butyl methyl ether were added to the reaction mixture and the organic layer was separated. The obtained organic layer was sequentially washed with water (twice) and brine. After drying over anhydrous magnesium sulfate, the organic layer was concentrated under reduced pressure. The obtained residue was purified by silica column chromatography (carrier: Wakogel™ C-200; elution solvent:heptane:ethyl acetate 49:1→19:1) to obtain the title compound (317 mg). The property values of the obtained compound are as follows; 1H-NMR (CDCl3) δ (ppm): 1.32 (dd, J=7.6, 5.2 Hz, 2H), 1.72 (dd, J=7.6, 5.2 Hz, 2H), 2.34 (s, 3H), 7.20 (s, 1H), 7.43 (s, 1H).

Workup

  1. customthe organic layer was separated
  2. washThe obtained organic layer was sequentially washed with water (twice) and brine
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. concentrationthe organic layer was concentrated under reduced pressure
  5. customThe obtained residue was purified by silica column chromatography (carrier: Wakogel™ C-200; elution solvent:heptane:ethyl acetate 49:1→19:1)

Sources & evidence

ORD record
ord-43b2cee6111743a8ae97c7e572cf04da
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

Loading…