2-Bromopropane → 2-(4-Methoxyphenyl)-3-methylbutyronitrile

HRID 354731Notes

Reaction equation

HRID 354731 reaction equation
[CH:1](Br)([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]#[N:22])=[CH:16][CH:15]=1>O>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]([CH:1]([CH3:3])[CH3:2])[C:21]#[N:22])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 8471TriethylamineHCID 66031Benzeneacetonitrile, 4-methoxy-

Product 1

HCID 130590562-(4-Methoxyphenyl)-3-methylbutyronitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture comprising: isopropyl bromide, sodium hydroxide pels, and optionally the catalyst triethylamine (i.e., approximately 0.5 to 12 mol or weight percent) is stirred and heated to 50°-60° C. Over approximately a 30-minute period 4-methoxyphenylacetonitrile is added to the reaction mixture. Following this addition, the mixture is stirred and heated at reflux for several hours. After cooling, water is added to the reaction mixture which is then stirred briefly. The organic phase containing the product is then separated. This solution can be used in subsequent reaction steps or the product can be isolated by removal of the solvents.

Workup

  1. temperatureheated to 50°-60° C
  2. additionthis addition
  3. temperatureheated
  4. temperatureat reflux for several hours
  5. temperatureAfter cooling
  6. stirringis then stirred briefly
  7. additionThe organic phase containing the product
  8. customis then separated
  9. customThis solution can be used in subsequent reaction steps
  10. customthe product can be isolated by removal of the solvents

Sources & evidence

ORD record
ord-359fa1d94d9245259e56683cb0310e13
Source dataset
uspto-grants-1983_03
Patent number
US04377531

Reaction notes

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