Water → 3-(2-Bromo-4,5-dimethoxyphenyl)propanenitrile

HRID 1624863Notes

Reaction equation

HRID 1624863 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]#[N:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C([O-])(=O)C.[Na+].[Br:20]Br.O>C(O)(=O)C>[Br:20][C:6]1[CH:7]=[C:8]([O:9][CH3:10])[C:3]([O:2][CH3:1])=[CH:4][C:5]=1[CH2:11][CH2:12][C:13]#[N:14]

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 3199323-(3,4-Dimethoxyphenyl)propanenitrileHCID 517045Sodium Acetate

Product 1

HCID 3204113-(2-Bromo-4,5-dimethoxyphenyl)propanenitrileYield 65.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a mixture of 21 g of 3-(3,4-dimethoxyphenyl)propanenitrile, 10.3 g of sodium acetate and 400 mL of acetic acid there are added 20 g of dibromine in 50 mL of acetic acid. The resulting reaction mixture is stirred overnight and then poured into water and extracted with benzene. The organic phase is washed with aqueous sodium thiosulphate solution and then with water, dried over sodium sulphate and concentrated under reduced pressure. The crude reaction product is purified on a silica column (eluant: benzene), and the product obtained is recrystallised from ethanol to yield 19.3 g of the expected product.

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted with benzene
  3. washThe organic phase is washed with aqueous sodium thiosulphate solution
  4. dry with materialwith water, dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude reaction product
  7. customis purified on a silica column (eluant: benzene)
  8. customthe product obtained
  9. customis recrystallised from ethanol

Sources & evidence

ORD record
ord-382adc58b35b49a89d2035fecd30b336
Source dataset
uspto-grants-2014_07
Patent number
US08779122B2

Reaction notes

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