Benzoyl Peroxide → 1-[3-Bromo-4-(bromomethyl)-5-chloro-2-methoxyphenyl]ethanone

HRID 510829Notes

Reaction equation

HRID 510829 reaction equation
[Br:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8].[Br:15]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([Cl:9])[C:7]=1[CH2:8][Br:15]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 866667591-(3-Bromo-5-chloro-2-methoxy-4-methylphenyl)ethanone

Product 1

HCID 866667651-[3-Bromo-4-(bromomethyl)-5-chloro-2-methoxyphenyl]ethanone

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 1-(3-bromo-5-chloro-2-methoxy-4-methylphenyl)ethanone (3.3 g, 12 mmol), N-bromosuccinimide (2.2 g, 13 mmol), and benzoyl peroxide (0.15 g, 0.60 mmol) in carbon tetrachloride (50 mL) was heated at reflux overnight. The mixture was cooled to room temperature and concentrated. The resulting residue was diluted with ethyl acetate and washed with water. The organic layers were dried over magnesium sulfate and evaporated to dryness. The crude product was used directly in next step. LCMS calculated for C10H10Br2ClO2 (M+H)+: m/z=355.1. found: 355.1.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated
  4. additionThe resulting residue was diluted with ethyl acetate
  5. washwashed with water
  6. dry with materialThe organic layers were dried over magnesium sulfate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-fe69af24a12f4c9b90fea368797324c4
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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