1-Bromo-3-chloropropane → 1-[4-(3-Chloropropoxy)-3,5-difluorophenyl]ethanone

HRID 1186866Notes

Reaction equation

HRID 1186866 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([F:9])[C:7]=1[OH:8].Br[CH2:14][CH2:15][CH2:16][Cl:17].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Cl:17][CH2:16][CH2:15][CH2:14][O:8][C:7]1[C:2]([F:1])=[CH:3][C:4]([C:10](=[O:12])[CH3:11])=[CH:5][C:6]=1[F:9]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 151513381-(3,5-Difluoro-4-hydroxyphenyl)ethan-1-one

Product 1

HCID 596519231-[4-(3-Chloropropoxy)-3,5-difluorophenyl]ethanoneYield 110.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1-(3,5-difluoro-4-hydroxyphenyl)ethanone (8.1 g, 47 mmol), 3-bromo-1-chloropropane (14.7 g, 93 mmol) and K2CO3 (21.3 g, 154 mmol) in acetone (120 mL) was stirred at reflux for 20 h. The reaction was cooled to rt and concentrated at reduced pressure, then partitioned between water and methylene chloride. The aqueous layer was extracted twice with methylene chloride to obtain 1-[4-(3-chloropropoxy)-3,5-difluoro-phenyl]ethanone (12.9 g, quantitative yield); MS m/z 249 (M+H).

Workup

  1. temperatureat reflux for 20 h
  2. concentrationconcentrated at reduced pressure
  3. custompartitioned between water and methylene chloride
  4. extractionThe aqueous layer was extracted twice with methylene chloride

Sources & evidence

ORD record
ord-d3359ebd13a9426c9bd4d8891a9da997
Source dataset
uspto-grants-2014_03
Patent number
US08673916B2

Reaction notes

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