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

HRID 1285389Notes

Reaction equation

HRID 1285389 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. After the inorganic salt was filtered off, the solvent was distilled off and the residue was dissolved in chloroform. The solution was chromatographed on a column of silica gel (80 g) and eluted with a solution of petroleum ether-ethyl acetate (10:1) to give 3.06 g of 3-(2-chloro-4-cyanophenoxy)propyl chloride as a colorless oil.

Workup

  1. filtrationAfter the inorganic salt was filtered off
  2. distillationthe solvent was distilled off
  3. dissolutionthe residue was dissolved in chloroform
  4. customThe solution was chromatographed 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-868a893f4d104fbeace962d8246611cc
Source dataset
uspto-grants-1986_01
Patent number
US04567201

Reaction notes

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