Ethyl Bromide → HCID 15628332, compound

HRID 1702467Notes

Reaction equation

HRID 1702467 reaction equation
[CH2:1](Br)[CH3:2].[CH2:4]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]#[N:16])=[CH:10][CH:9]=1)[CH:5]([CH3:7])[CH3:6].[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[CH2:4]([C:8]1[CH:9]=[CH:10][C:11]([CH:14]([CH2:1][CH3:2])[C:15]#[N:16])=[CH:12][CH:13]=1)[CH:5]([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 14798Sodium HydroxideHCID 170426(4-Isobutylphenyl)acetonitrile

Product 1

HCID 15628332HCID 15628332, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst

Conditions

Temperature
40 °C

Procedure

550 g of ethyl bromide are added drop-wise to 470 g of 4-isobutylphenyl acetonitrile, 1550 g of a 50% solution of sodium hydroxide and 11.4 g of triethylbenzyl ammonium chloride. The addition is complete within 2 hours. During this addition, the temperature must be controlled such that it does not exceed 40° C. The mixture is agitated for 10 hours at 40° C. After cooling of the mixture, the alkaline phase is discarded and the organic layer is washed with water until neutral. Fractionation yields 536 g of crude 2-(4-isobutylphenyl)butyronitrile.

Workup

  1. additionThe addition
  2. additionDuring this addition
  3. customdoes not exceed 40° C
  4. temperatureAfter cooling of the mixture
  5. washthe organic layer is washed with water until neutral

Sources & evidence

ORD record
ord-5f366e1d441e44af8264719bd994f9f9
Source dataset
uspto-grants-1983_04
Patent number
US04381313

Reaction notes

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