Benzoyl Peroxide → Methyl 5-bromo-2-(bromomethyl)benzoate

HRID 403930

Reaction equation

HRID 403930 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C1C(=O)N([Br:38])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:12][Br:38])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 316201Methyl 5-bromo-2-methylbenzoate

Product 1

HCID 12929136Methyl 5-bromo-2-(bromomethyl)benzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 5-bromo-2-methylbenzoate (1.0 g, 0.45 mol) was dissolved in carbon tetrachloride (15 mL) to which benzoyl peroxide (40 mg) and NBS (1.49 g, 0.83 mol) were added and the reaction mixture was refluxed at 80° C. After completion of the reaction, the reaction mixture was cooled to room temperature and filtered through celite. The filtrate was concentrated to obtain a crude material containing 95% mono bromo and 5% dibromo product. The crude material was used directly for the preparation of compound of example 329 without purification.

Workup

  1. additionwere added
  2. customAfter completion of the reaction
  3. temperaturethe reaction mixture was cooled to room temperature
  4. filtrationfiltered through celite
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-7875f7d7fe034f53bb73702107925f53
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Linked notes

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