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

HRID 354732Notes

Reaction equation

HRID 354732 reaction equation
[CH:1](Br)([CH3:3])[CH3:2].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]#[N:15])=[CH:9][CH:8]=1>O>[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH:1]([CH3:3])[CH3:2])[C:14]#[N:15])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 63582-BromopropaneHCID 66031Benzeneacetonitrile, 4-methoxy-

Product 1

HCID 130590562-(4-Methoxyphenyl)-3-methylbutyronitrileYield 99.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred suspension of sodium hydroxide pels (320.0 g; 8.0 mol) in isopropyl bromide (492.0 g; 4.0 mol) is added 4-methoxyphenylacetonitrile (294.3 g; 2.0 mol) over a 30-minute period at a temperature of 50°-55° C. Following this addition the reaction mixture is stirred at reflux (68°-74° C.) for 4 hours. It is then cooled to 50° C. and water (498 ml) is added. The mixture is subsequently stirred for 15 minutes with cooling. The aqueous and organic phases are then separated and the excess isopropyl bromide is removed from the organic phase by distillation. The resulting product (367.88 g of 2-(4-methoxyphenyl)-3-methylbutyronitrile) is 96.9% pure and corresponds to a real yield of 99.1%. The results of this experiment are included in Table Ia under No. 7.

Workup

  1. additionthis addition the reaction mixture
  2. temperatureat reflux (68°-74° C.) for 4 hours
  3. stirringThe mixture is subsequently stirred for 15 minutes
  4. temperaturewith cooling
  5. customThe aqueous and organic phases are then separated
  6. customthe excess isopropyl bromide is removed from the organic phase by distillation
  7. customThe results of this experiment

Sources & evidence

ORD record
ord-a95bcfc508da40b5a4f025acd32c0c2b
Source dataset
uspto-grants-1983_03
Patent number
US04377531

Reaction notes

Loading…