4-Methylbenzophenone → 4-(Bromomethyl)benzophenone

HRID 1634573Notes

Reaction equation

HRID 1634573 reaction equation
[CH3:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[Br:16]Br>C1C=CC=CC=1>[Br:16][CH2:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 86524-MethylbenzophenoneHCID 24408Bromine

Product 1

HCID 1229514-(Bromomethyl)benzophenone

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

4-Methylbenzophenone, 750 g (3.82 moles), is added to a 5 liter Morton flask equipped with an overhead stirrer and dissolved in 2850 ml of benzene. The solution is then heated to reflux, followed by the dropwise addition of 610 g (3.82 moles) of bromine in 330 ml of benzene. The addition rate is approximately 1.5 ml/min and the flask is illuminated with a 90 watt (90 joule/sec) halogen spotlight to initiate the reaction. A timer is used with the lamp to provide a 10% duty cycle (on 5 seconds, off 40 seconds), followed in one hour by a 20% duty cycle (on 10 seconds, off 40 seconds). After cooling, the reaction mixture is washed with 10 g of sodium bisulfite in 100 ml of water, followed by washing with 3×200 ml of water. The product is dried over sodium sulfate and recrystallized twice from toluene/hexane (⅓ by volume). The final compound is stored for use in the preparation of a reagent suitable for derivatization of nucleic acids as described in Example 4(b).

Workup

  1. customequipped with an overhead stirrer
  2. temperatureThe solution is then heated
  3. temperatureto reflux
  4. customthe reaction
  5. customto provide a 10% duty cycle (on 5 seconds, off 40 seconds)
  6. temperatureAfter cooling
  7. washthe reaction mixture is washed with 10 g of sodium bisulfite in 100 ml of water
  8. washby washing with 3×200 ml of water
  9. dry with materialThe product is dried over sodium sulfate
  10. customrecrystallized twice from toluene/hexane (⅓ by volume)
  11. customThe final compound is stored for use in the preparation of a reagent suitable for derivatization of nucleic acids

Sources & evidence

ORD record
ord-476eb3a2166d4b8b9a137536225f8921
Source dataset
uspto-grants-2003_01
Patent number
US06506895B2

Reaction notes

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