2-Bromopropane → alpha-Isopropyl-3-fluoro-4-methoxyphenylacetonitrile

HRID 2050097Notes

Reaction equation

HRID 2050097 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11]#[N:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].Br[CH:14]([CH3:16])[CH3:15].[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[CH:14]([CH:10]([C:4]1[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([F:1])[CH:3]=1)[C:11]#[N:12])([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 63582-BromopropaneHCID 14798Sodium HydroxideHCID 1362513-Fluoro-4-methoxyphenylacetonitrile

Product 1

HCID 20343280alpha-Isopropyl-3-fluoro-4-methoxyphenylacetonitrileYield 82.3%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

A mixture of 3-fluoro-4-methoxyphenylacetonitrile (30 g, 0.18 mol), 2-bromopropane (27.7 g, 0.225 mol), benzyltriethylammonium chloride (2.3 g, 0.01 mol) and sodium hydroxide solution (50%, 66 ml) is heated at 55° for 1 hour and cooled. The mixture is diluted with water, extracted with ether, washed with water, 1 NHCl, water, and dried (Na2SO4). Evaporation gives the product as a brown oil (30.7 g). NMR spectrum shows the benzylic proton as a doublet at 3.6 δ.

Workup

  1. temperatureis heated at 55° for 1 hour
  2. temperaturecooled
  3. extractionextracted with ether
  4. washwashed with water, 1 NHCl, water
  5. dry with materialdried (Na2SO4)
  6. customEvaporation

Sources & evidence

ORD record
ord-e6ff7ff636c642b09b057d0f01e5e20d
Source dataset
uspto-grants-1980_04
Patent number
US04199595

Reaction notes

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