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

HRID 2042603Notes

Reaction equation

HRID 2042603 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-2bd14c775b82437689d3815006cfe6b3
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

Loading…