Water → HCID 68974851, compound

HRID 657551Notes

Reaction equation

HRID 657551 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([CH2:10][CH2:11][C:12]#[N:13])=[CH:5][CH:4]=1.C([O-])(=O)C.[Na+].[Br:19]Br.O>C(O)(=O)C>[Br:19][C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][C:12]#[N:13])[CH:7]=[C:8]([CH3:9])[C:3]=1[O:2][CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 517045Sodium AcetateHCID 12386402HCID 12386402, compound

Product 1

HCID 68974851HCID 68974851, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

62.8 g (358.4 mmol) of 3-(4-methoxy-5-methylphenyl)propanenitrile are dissolved in 390 mL of acetic acid. There are then added, all at once, 58.8 g (716.8 mmol/2 eq.) of sodium acetate and then, dropwise, 20.2 mL (394.2 mmol/1.1 eq.) of bromine, and stirring is carried out at ambient temperature overnight. The reaction mixture is then poured into 2 liters of water, and the aqueous phase is extracted 3 times with 500 mL of dichloromethane. The combined organic phases are washed successively with 500 mL of water, 500 mL of saturated aqueous sodium hydrogen carbonate solution and 500 mL of water, and are dried over magnesium sulphate. After concentration, the expected product is collected.

Workup

  1. additionThere are then added
  2. extractionthe aqueous phase is extracted 3 times with 500 mL of dichloromethane
  3. washThe combined organic phases are washed successively with 500 mL of water, 500 mL of saturated aqueous sodium hydrogen carbonate solution and 500 mL of water
  4. dry with materialare dried over magnesium sulphate
  5. concentrationAfter concentration
  6. customthe expected product is collected

Sources & evidence

ORD record
ord-fb23660fbff147b2b03a12c2599f22d8
Source dataset
uspto-grants-2011_12
Patent number
US08076325B2

Reaction notes

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