Benzoyl Peroxide → 2-Methyl-3-bromo-3-phenyloctan-4-one

HRID 1958559Notes

Reaction equation

HRID 1958559 reaction equation
[CH3:1][CH:2]([CH:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5](=[O:10])[CH2:6][CH2:7][CH2:8][CH3:9])[CH3:3].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C1C(=O)N([Br:42])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[CH3:1][CH:2]([C:4]([Br:42])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5](=[O:10])[CH2:6][CH2:7][CH2:8][CH3:9])[CH3:3]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 598649852-Methyl-3-phenyloctan-4-one

Product 1

HCID 598649412-Methyl-3-bromo-3-phenyloctan-4-one

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a magnetically stirred solution of 2-methyl-3-phenyloctan-4-one (Intermediate IIa-1) (4.31 gram, 0.02 mol) in CCl4 (40 ml) was added a catalytic amount of dibenzoyl peroxide and NBS (6.56 gram). The resulting mixture was heated for 6 hours at reflux temperature. The obtained mixture was allowed to attain room temperature. The formed precipitate was removed by filtration. The filtrate was concentrated to give crude 2-methyl-3-bromo-3-phenyloctan-4-one (intermediate IIb-1)—contaminated with some starting material—as a dark-colored oil (6.77 gram). 1H-NMR (400 MHz, CDCl3) Characteristic signals: δ 0.68 (d, J=6, 3H), 0.78 (t, J=7, 3H), 1.08 (d, J=6, 3H).

Workup

  1. temperatureThe resulting mixture was heated for 6 hours
  2. temperatureat reflux temperature
  3. customto attain room temperature
  4. customThe formed precipitate was removed by filtration
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-d56faf7de1984d74a32513b4c5ce36b3
Source dataset
uspto-grants-2013_04
Patent number
US08410135B2

Reaction notes

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