1-Bromopropane → HCID 12343240, compound

HRID 2073896Notes

Reaction equation

HRID 2073896 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.Br[CH2:12][CH2:13][CH3:14].[OH-].[Na+]>[Br-].C([N+](CC)(CC)CC)C.CS(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:12][CH2:13][CH3:14])[C:9]#[N:10])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 78401-BromopropaneHCID 14798Sodium HydroxideHCID 68016Benzeneacetonitrile, 4-fluoro-

Product 1

HCID 12343240HCID 12343240, compoundYield 35.1%

Reagents, catalysts & solvents 2

HCID 6285Tetraethylammonium BromideCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

To 50.0 gm (0.37 mol) of 4-fluorophenylacetonitrile, 0.6 gm of tetraethyl ammonium bromide, 50 gm (0.407 mol) of 1-bromopropane and 50 ml of DMSO was added 35.5 gm (0.44 mol) of 50% (w/w) sodium hydroxide at room temperature. After the addition was complete, the reaction was stirred at 50°-60° C. for 3 hours. The reaction mixture was extracted with ether, the organic phase washed with water and then 10% (w/w) hydrochloric acid. The ether was dried, filtered and distilled to give 23 grams of the product (b.p. 105°-110° C. at 5 mm).

Workup

  1. additionAfter the addition
  2. extractionThe reaction mixture was extracted with ether
  3. washthe organic phase washed with water
  4. dry with materialThe ether was dried
  5. filtrationfiltered
  6. distillationdistilled

Sources & evidence

ORD record
ord-27b4ed3ce0744bda8e9cd46447eca41f
Source dataset
uspto-grants-1990_04
Patent number
US04920139

Reaction notes

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