1-Bromo-3-chloropropane → HCID 20197663, compound

HRID 652456Notes

Reaction equation

HRID 652456 reaction equation
[Br: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>[Br: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 753413-Bromo-4-hydroxybenzonitrile

Product 1

HCID 20197663HCID 20197663, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-bromo-4-cyanophenol (3.96 g), 3-bromopropyl chloride (3.46 g), dimethylformamide (20 ml) and anhydrous potassium carbonate (3 g) was heated at 100° C. for 0.5 hour. The inorganic salt was filtered off, and the filtrate was concentrated. The residue was chromatographed on a column of silica gel (90 g), and eluted with a solution of n-hexane-chloroform-acetone (20:10:1) to give 3-(2-bromo-4-cyanophenoxy)propyl chloride as a colorless oil (4.15 g).

Workup

  1. filtrationThe inorganic salt was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was chromatographed on a column of silica gel (90 g)
  4. washeluted with a solution of n-hexane-chloroform-acetone (20:10:1)

Sources & evidence

ORD record
ord-5aa517317e3542b298d90c463899e1cf
Source dataset
uspto-grants-1987_06
Patent number
US04672073

Reaction notes

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