1-Bromo-3-chloropropane → HCID 13912832, compound

HRID 652454Notes

Reaction equation

HRID 652454 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][C:3]=1[OH:10].Br[CH2:12][CH2:13][CH2:14][Cl:15].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][C:3]=1[O:10][CH2:12][CH2:13][CH2:14][Cl:15]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 2735739Benzonitrile, 3-chloro-4-hydroxy-

Product 1

HCID 13912832HCID 13912832, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-4-cyanophenol (2.15 g), 3-bromo-1-chloropropane (2.3 g), dimethylformamide (3 ml) and potassium carbonate (1.5 g) was heated at 100° C. for one hour. The inorganic salt was then filtered off and the solvent was distilled off. The residue was dissolved in chloroform, chromatographed on a column of silica gel (80 g), and eluted with a solution of petroleum ether-ethyl acetate (10:1) to give 3-(2-chloro-4-cyanophenoxy)propyl chloride as a colorless oil (3.06 g).

Workup

  1. filtrationThe inorganic salt was then filtered off
  2. distillationthe solvent was distilled off
  3. dissolutionThe residue was dissolved in chloroform
  4. customchromatographed on a column of silica gel (80 g)
  5. washeluted with a solution of petroleum ether-ethyl acetate (10:1)

Sources & evidence

ORD record
ord-1d490680f71445f294f8123e100d186e
Source dataset
uspto-grants-1987_06
Patent number
US04672073

Reaction notes

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