Diethyl Ether → 1-(3-Bromo-2-methylphenyl)ethanone

HRID 258908Notes

Reaction equation

HRID 258908 reaction equation
[Mg].CI.[CH3:4][C:5]1[C:10]([Br:11])=[CH:9][CH:8]=[CH:7][C:6]=1C#N.CC[O:16][CH2:17][CH3:18]>>[Br:11][C:10]1[C:5]([CH3:4])=[C:6]([C:17](=[O:16])[CH3:18])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 4

HCID 3283Diethyl Ether2×HCID 6328Methyl iodideHCID 5462224MagnesiumHCID 234335373-Bromo-2-methylbenzonitrile

Product 1

HCID 204801311-(3-Bromo-2-methylphenyl)ethanone

Conditions

Temperature
0 °C

Procedure

To a stirred and refluxing Grignard-complex, previously prepared starting from 7.3 parts of magnesium, 52.6 parts of methyl iodide in 160 parts of ether, is added dropwise a solution of 19.6 parts of 3'-bromo-2'-methylbenzonitrile in 40 parts of ether. Upon completion, stirring at reflux is continued for 20 hours. The reaction mixture is cooled to 0° C and poured onto 500 parts of ice-water while stirring vigorously. The ethereal phase is separated, dried and evaporated. The residue is boiled in 60 parts of a 6N hydrochloric acid solution for 10 minutes. The separated oil is extracted with ether. The extract is washed with water, dried and evaporated. The residue is distilled, yielding 3'-bromo-2'-methylacetophenone; bp. 125°-128° C at 10 mm. pressure.

Workup

  1. temperaturerefluxing Grignard-complex
  2. custompreviously prepared
  3. stirringUpon completion, stirring
  4. temperatureat reflux
  5. stirringwhile stirring vigorously
  6. customThe ethereal phase is separated
  7. customdried
  8. customevaporated
  9. waitThe residue is boiled in 60 parts of a 6N hydrochloric acid solution for 10 minutes
  10. extractionThe separated oil is extracted with ether
  11. washThe extract is washed with water
  12. customdried
  13. customevaporated
  14. distillationThe residue is distilled

Sources & evidence

ORD record
ord-3f6c5b831b754f8ba0677283f8d9a899
Source dataset
uspto-grants-1977_07
Patent number
US04035376

Reaction notes

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