Ethyl Bromide → HCID 11435291, compound

HRID 1868656Notes

Reaction equation

HRID 1868656 reaction equation
[H-].[Na+].Br[CH2:4][CH3:5].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]#[N:15])=[CH:9][CH:8]=1>CN1C(=O)CCC1.CCOCC>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH2:4][CH3:5])[C:14]#[N:15])=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 2415824-Chlorobenzyl cyanide

Product 1

HCID 11435291HCID 11435291, compoundYield 51.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of NaH (4.0 g, 99 mmol) in 50 mL NMP stirred at 0° C., was treated dropwise with a mixture of bromoethane (11 g, 99 mmol) and 2-(4-chlorophenyl)acetonitrile (15 g, 99 mmol) in 20 mL ether. The mixture was stirred at room temperature for 2 hours, cooled to 0° C., and quenched carefully with H2O. The resulting mixture was neutralized with 10% HCl to a pH of 5. The mixture was extracted with ether (3×50 mL). The combined organic layers were washed with brine (30 mL), dried over anhydrous Na2SO4, concentrated in vacuo, and purified by column chromatography eluting with 5% EtOAc/hexane to give 9.1 g of the product as a pale yellow oil.

Workup

  1. stirringThe mixture was stirred at room temperature for 2 hours
  2. temperaturecooled to 0° C.
  3. customquenched carefully with H2O
  4. extractionThe mixture was extracted with ether (3×50 mL)
  5. washThe combined organic layers were washed with brine (30 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo
  8. custompurified by column chromatography
  9. washeluting with 5% EtOAc/hexane

Sources & evidence

ORD record
ord-504334d20d794072ade4a19712f40965
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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