Bromine → 1-[4-(Bromomethyl)phenyl]-2,2-dimethylpropan-1-one

HRID 1657966Notes

Reaction equation

HRID 1657966 reaction equation
[C:1]([C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[Br:14]Br>>[Br:14][CH2:13][C:10]1[CH:11]=[CH:12][C:7]([C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 24408BromineHCID 1980932,2-Dimethyl-1-(4-methylphenyl)-1-propanone

Product 1

HCID 128310071-[4-(Bromomethyl)phenyl]-2,2-dimethylpropan-1-one

Conditions

Temperature
150 °C

Procedure

To a flask equipped with stirrer, thermometer, condenser, addition funnel and heating mantle, there is added 44.0 grams (0.25 mole) of p-pivaloyl toluene at a temperature of 150°C. There is then added dropwise, while maintaining the temperature at 150°C., 40 grams (0.25 mole) of liquid bromine over a period of 10 to 15 minutes. The mixture is then stirred for an additional 10 minutes again while maintaining the temperature at about 140° to 150°C. The resulting brown liquid is cooled and degassed with nitrogen to obtain α-bromo-4-pivaloyl toluene in liquid form, b.p. 124° to 132°C. at 0.3 mm.

Workup

  1. customTo a flask equipped with stirrer
  2. additionthermometer, condenser, addition funnel
  3. temperatureheating mantle, there
  4. additionThere is then added dropwise
  5. temperaturewhile maintaining the temperature at about 140° to 150°C
  6. temperatureThe resulting brown liquid is cooled
  7. customdegassed with nitrogen

Sources & evidence

ORD record
ord-8c72482cf8b142f493bd8b0316201b24
Source dataset
uspto-grants-1976_06
Patent number
US03962342

Reaction notes

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