Benzoyl Peroxide → Methyl 4-bromo-2-(bromomethyl)benzoate

HRID 403953Notes

Reaction equation

HRID 403953 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:12])[CH:3]=1.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:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH2:12][Br:38])[CH:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 22031226Methyl 4-bromo-2-methylbenzoate

Product 1

HCID 22031079Methyl 4-bromo-2-(bromomethyl)benzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 4-bromo-2-methylbenzoate (9.6 g, 0.42 mol) was dissolved in carbon tetrachloride (150 mL). Benzoyl peroxide (250 mg) and NBS (7.6 g, 0.42 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 85% mono bromo and 10% dibromo product. The crude product obtained was used directly, without purification for preparation of compound of example 359.

Workup

  1. customAfter completion of the reaction
  2. temperaturethe reaction mixture was cooled to room temperature
  3. filtrationfiltered through celite
  4. concentrationThe filtrate was concentrated
  5. customto obtain a crude material
  6. additioncontaining 85% mono bromo and 10% dibromo product

Sources & evidence

ORD record
ord-25965fc922b842b0a7446b410689023f
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Reaction notes

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