Phenethyl bromide → alpha-Phenethyl-2,4-dichlorobenzyl cyanide

HRID 616391Notes

Reaction equation

HRID 616391 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:5]=1[CH2:6][C:7]#[N:8].O1CCCC1.[CH2:19](Br)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O>[CH2:19]([CH:6]([C:7]#[N:8])[C:5]1[CH:9]=[CH:10][C:11]([Cl:13])=[CH:12][C:4]=1[Cl:3])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 7666Phenethyl bromideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 805662,4-Dichlorophenylacetonitrile

Product 1

HCID 12391165alpha-Phenethyl-2,4-dichlorobenzyl cyanide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

Sodium hydride (0.13 mole as a 50% dispersion in mineral oil) is washed with 100 ml. of dry n-hexane to remove the mineral oil, then blanketed with dry nitrogen and suspended in 250 ml. of freshly distilled tetrahydrofuran. To this sodium hydride suspension is added dropwise at room temperature a solution of 2,4-dichlorobenzyl cyanide (25g., 0.13 mole) dissolved in 100 ml. of tetrahydrofuran. When the addition is completed, the temperature is maintained at 30° C. for an additional 0.5 hours. A solution of phenethylbromide (26g., 0.14 mole) is then added dropwise and the resultant reaction mixture is stirred at 40° C. overnight under nitrogen. The reaction mixture is poured into 1 liter of water and extracted with (3 × 200 ml.) of ether. The combined ether extracts are washed with water, dilute hydrochloric acid, saturated sodium bicarbonate solution, saturated sodium chloride solution and dried over magnesium sulfate. The solvent is evaporated and the crude product distilled (144°-56°/0.03 mm) to give 26.6g. (70.5%) of product, which is identified by nmr.

Workup

  1. washSodium hydride (0.13 mole as a 50% dispersion in mineral oil) is washed with 100 ml
  2. customof dry n-hexane to remove the mineral oil
  3. dissolutiondissolved in 100 ml
  4. additionWhen the addition
  5. customthe resultant reaction mixture
  6. extractionextracted with (3 × 200 ml.) of ether
  7. washThe combined ether extracts are washed with water, dilute hydrochloric acid, saturated sodium bicarbonate solution, saturated sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent is evaporated
  10. distillationthe crude product distilled (144°-56°/0.03 mm)
  11. customto give 26.6g

Sources & evidence

ORD record
ord-4513aa3cc6744342863d8c54912eec1a
Source dataset
uspto-grants-1978_02
Patent number
US04073921

Reaction notes

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