Benzene → 4-Chloro-1-(4-chlorophenyl)-2-fluorobutan-1-one

HRID 704525Notes

Reaction equation

HRID 704525 reaction equation
Br[CH:2]([C:6]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)=[O:7])[CH2:3][CH2:4][Cl:5].[F-:15].[K+].C1OCCOCCOCCOCCOCCOC1.C1C=CC=CC=1>O>[F:15][CH:2]([C:6]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)=[O:7])[CH2:3][CH2:4][Cl:5]

Participants

6

Reactant 4

HCID 241BenzeneHCID 2855718-Crown-6HCID 1071672-Bromo-4-chloro-1-(4-chlorophenyl)butan-1-oneHCID 522689Potassium Fluoride

Product 1

HCID 137116864-Chloro-1-(4-chlorophenyl)-2-fluorobutan-1-oneYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 68 g of 4-chlorophenyl 1-bromo-3chloropropyl ketone, 27.5 g of dry potassium fluoride, 11 g of 18-crown-6 and 200 ml of dry benzene is heated under reflux for 8 hours. Thereafter, 200 ml of water are added, and the organic phase is separated off, washed several times with water, dried over sodium sulphate and evaporated down in vacuo. The residue is stirred with light benzine, with the addition of a small amount of toluene. After the resulting solid has been filtered off under suction and drying has been carried out, 28.5 g (53% of theory) of 4-chlorophenyl 1-fluoro-3-chloropropyl ketone of melting point 53° C. are obtained. ##STR217##

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 8 hours
  3. customthe organic phase is separated off
  4. washwashed several times with water
  5. dry with materialdried over sodium sulphate
  6. customevaporated down in vacuo
  7. filtrationAfter the resulting solid has been filtered off under suction
  8. customdrying

Sources & evidence

ORD record
ord-17543b726cd444589f22ae8699a4ae46
Source dataset
uspto-grants-1991_01
Patent number
US04988382

Reaction notes

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