Hydrogen Bromide → 5-Bromo-2-(3,4-dimethoxyphenyl)-2-isopropylpentanenitrile

HRID 21816Notes

Reaction equation

HRID 21816 reaction equation
[CH2:1]([C:4]([C:18]#[N:19])([CH:15]([CH3:17])[CH3:16])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1)[CH:2]=[CH2:3].N(C(C)(C)C#N)=NC(C)(C)C#N.[BrH:32].C(=O)([O-])[O-].[K+].[K+]>C1CCCCC1.CCCCCC>[Br:32][CH2:3][CH2:2][CH2:1][C:4]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1)([CH:15]([CH3:17])[CH3:16])[C:18]#[N:19]

Participants

7

Reactant 4

HCID 260Hydrogen Bromide2×HCID 6547AzobisisobutyronitrileHCID 11430Potassium CarbonateHCID 13777671HCID 13777671, compound

Product 1

HCID 135355715-Bromo-2-(3,4-dimethoxyphenyl)-2-isopropylpentanenitrileYield 94%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8078CyclohexaneSolvent

Procedure

To a solution of 50 g of α-allyl-α-isopropyl-3,4-dimethoxy- benzyl cyanide and 2 g of azobisisobutyronitrile in 400 ml of cyclohexane (or n-hexane) gaseous hydrogen bromide was introduced for 70 minutes, when, according to GLC, the reaction mixture did not contain the starting allyl derivative. During the introduction of the hydrogen bromide, the reaction temperature raised to 40° C. The reaction mixture was neutralized with 200 ml of 30% solution of potassium carbonate. The separated cyclohexane solution of the product was washed with water until neutral pH. After drying and evaporating the solvent under diminished pressure, the crude product (61.7 g, 94%) was obtained, which could be used without purification in further reaction step.

Workup

  1. washThe separated cyclohexane solution of the product was washed with water until neutral pH
  2. customAfter drying
  3. customevaporating the solvent under diminished pressure

Sources & evidence

ORD record
ord-b259bfe320c6429e97d7d310b46f9bcf
Source dataset
uspto-grants-1995_06
Patent number
US05424456

Reaction notes

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