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

HRID 354733Notes

Reaction equation

HRID 354733 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-methylbutyronitrileYield 105.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

To a stirred mixture of isopropyl bromide (246.0 g; 2.0 mol), triethylamine (160.0 g; 4.0 mol), and solid sodium hydroxide pels (160.0 g; 4.0 mol) is added 4-methoxyphenylacetonitrile (147.18 g, 95% pure=139.85 g; 0.95 mol) over a 30-minute period at 60° C. Following this addition the reaction mixture is stirred at 68°-74° C. for 6 hours. The reaction mixture is then cooled to 45° C. and water (205 ml) is added. The mixture is subsequently stirred for 15 minutes with cooling. The organic and aqueous phases are then separated and the excess isopropyl bromide and triethylamine is distilled from the organic phase. This method gives 189.7 g of product which is 92.6% pure. This corresponds to an effective yield of 98.7%.

Workup

  1. additionthis addition the reaction mixture
  2. stirringThe mixture is subsequently stirred for 15 minutes
  3. temperaturewith cooling
  4. customThe organic and aqueous phases are then separated
  5. distillationthe excess isopropyl bromide and triethylamine is distilled from the organic phase

Sources & evidence

ORD record
ord-ab2f50249d894005a894e20ee150fdc7
Source dataset
uspto-grants-1983_03
Patent number
US04377531

Reaction notes

Loading…