Benzoyl Peroxide → 4-(Bromomethyl)benzophenone

HRID 2192750Notes

Reaction equation

HRID 2192750 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]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.BrCC1C=CC(C2C=CC=CC=2C(C2C=CC=CC=2)=O)=CC=1>C(#N)C>[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

6

Reactant 4

HCID 7187Benzoyl PeroxideHCID 86524-MethylbenzophenoneHCID 67184N-bromobutanimideHCID 53630861HCID 53630861, compound

Product 1

HCID 1229514-(Bromomethyl)benzophenone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a 200-mL flask equipped with a reflux condenser were added 25.1 g of 4-methylbenzophenone (Aldrich), 22.8 g of N-bromosuccinimide (Wako Pure Chemical Industries, Ltd.), 0.54 g of benzoyl peroxide (containing 20% water, Wako Pure Chemical Industries, Ltd.), and 80 g of acetonitrile, which were heated to 80° C. and were made react under reflux for 2 hours. After cooling, the solvent was distilled away and the residue was recrystallized from 160 g of methanol, so that 26 g of intermediate (H10) (white crystals) was obtained. As a result of an analysis by 1H-NMR {300 MHz, CDCl3, δ (ppm): 7.9-7.7 (m, 4H), 7.6 (t, 1H), 7.55-7.4 (m, 4H), 4.5 (s, 2H)}, it was confirmed that this intermediate (H10) was 4-bromomethylphenylbenzophenone.

Workup

  1. customTo a 200-mL flask equipped with a reflux condenser
  2. customwere made react
  3. temperatureunder reflux for 2 hours
  4. temperatureAfter cooling
  5. distillationthe solvent was distilled away
  6. customthe residue was recrystallized from 160 g of methanol, so that 26 g of intermediate (H10) (white crystals)
  7. customwas obtained
  8. customAs a result of an analysis by 1H-NMR {300 MHz, CDCl3, δ (ppm)

Sources & evidence

ORD record
ord-9202445438fc4ab192fa79ff8a7b47c7
Source dataset
uspto-grants-2012_12
Patent number
US08329771B2

Reaction notes

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