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

HRID 1624857
Notes
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Reaction equation

HRID 1624857 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].C1C(=O)N([Br:22])C(=O)C1.O>CN(C=O)C>[Br:22][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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 3199323-(3,4-Dimethoxyphenyl)propanenitrile

Product 1

HCID 3204113-(2-Bromo-4,5-dimethoxyphenyl)propanenitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1 g (5.3 mmoles) of 3-(3,4-dimethoxyphenyl)propanenitrile in 42 mL of DMF is cooled to 0° C. To the resulting solution there is added, little by little, 0.93 g of NBS (5.2 mmoles, 1 eq.). After stirring for 30 minutes at 0° C., the reaction mixture is brought back to ambient temperature and stirred for two hours. It is then hydrolysed using 170 mL of water and extracted twice with 130 mL of ethyl acetate. The organic phases are collected and then washed, first with saturated aqueous Na2S2O5 solution and then with water. After evaporating off the solvent under reduced pressure, 1.29 g of a colourless oil which crystallises into a white solid are obtained.

Workup

  1. additionTo the resulting solution there is added
  2. customis brought back to ambient temperature
  3. stirringstirred for two hours
  4. extractionextracted twice with 130 mL of ethyl acetate
  5. customThe organic phases are collected
  6. washwashed, first with saturated aqueous Na2S2O5 solution
  7. customAfter evaporating off the solvent under reduced pressure, 1.29 g of a colourless oil which
  8. customcrystallises into a white solid
  9. customare obtained

Sources & evidence

ORD record
ord-a655c0a9287149348456602ed37746f2
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08779121B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes