1-Bromo-3-chloropropane → 2-(3-Chloropropoxy)benzonitrile

HRID 1709834Notes

Reaction equation

HRID 1709834 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9])#[N:2].Br[CH2:11][CH2:12][CH2:13][Cl:14].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.C(Cl)(Cl)Cl>[Cl:14][CH2:13][CH2:12][CH2:11][O:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:1]#[N:2]

Participants

6

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 119072-Hydroxybenzonitrile

Product 1

HCID 144071832-(3-Chloropropoxy)benzonitrileYield 97.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 2-cyanophenol (50.0 g, 0.42 mole), 1-bromo-3-chloropropane (67.7 g, 0.43 mole), and potassium carbonate (58.0 g, 0.42 mole) was heated overnight at gentle reflux in 500 ml of acetone. The reaction mixture was stripped to dryness and the residue was dissolved in chloroform. The chloroform layer was extracted several times with 5% sodium hydroxide. The chloroform layer was dried (anhydrous sodium sulfate), filtered, and the solvent was removed, to give a brown oil (80.09 g). A ten gram portion of this oil was subjected to flash chromatography on silica gel with 10% ethyl acetate-hexanes and 20% ethyl acetate-hexanes used for elution. Fractions were combined and solvent removed in vacuo. The clear oil obtained was dried 18 hrs in vacuo at room temperature and 8 hrs at 80° C. in vacuo. This furnished 5.24 g (50.0% yield--based on aliquot taken) of clear oil. 1H HMR (CDCl3); δ 2.1-2.5 (q, 2, --CH2), 3.8 (t, 2, --ClCH2), 4.2 (t, 2, --OCH2), 6.9 (m, 2, aromatic protons ortho and para to ether), 7.5 (m, 2, aromatic protons ortho and para to CN group).

Workup

  1. temperaturewas heated overnight
  2. extractionThe chloroform layer was extracted several times with 5% sodium hydroxide
  3. dry with materialThe chloroform layer was dried (anhydrous sodium sulfate)
  4. filtrationfiltered
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-c3e47b5dbc3e40cd99c68b3f386ef6d3
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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