Hydrochloric Acid → 1-(4-Bromo-3-methylphenyl)propan-1-one

HRID 584321Notes

Reaction equation

HRID 584321 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#N)=[CH:4][C:3]=1[CH3:10].[CH2:11]([Mg]Br)[CH3:12].Cl.[O:16]1CCOCC1>>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6](=[O:16])[CH2:11][CH3:12])=[CH:4][C:3]=1[CH3:10]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 27374944-Bromo-3-methylbenzonitrileHCID 178418443HCID 178418443, compound

Product 1

HCID 223456201-(4-Bromo-3-methylphenyl)propan-1-one

Conditions

Temperature
0 °C

Procedure

24.7 g (126 mmol) of 4-bromo-3-methylbenzonitrile are dissolved in 400 ml of anhydrous dioxane and the medium is then cooled to 0° C. 124 ml (372 mmol) of ethylmagnesium bromide are added dropwise and the medium is then warmed to room temperature and stirred for 4 hours. The reaction medium is treated with 250 ml of 3N HCl and then extracted with a water/ether mixture. A white solid is obtained after trituration from heptane (m=14.5 g, Y=52%).

Workup

  1. temperaturethe medium is then warmed to room temperature
  2. extractionextracted with a water/ether mixture
  3. customA white solid is obtained after trituration from heptane (m=14.5 g, Y=52%)

Sources & evidence

ORD record
ord-d49d561eb1aa4735bf945fe4cf30a623
Source dataset
uspto-grants-2005_08
Patent number
US06924400B2

Reaction notes

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