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

HRID 230234

Reaction equation

HRID 230234 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[CH3:11].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>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[CH2:11][Br:38]

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
100 °C

Procedure

5-Bromo-2-methyl-benzoic acid methyl ester (1.31 g, 5.72 mmol) was dissolved in carbon tetrachloride (40 mL). Benzoyl peroxide (10-20 mg) and NBS (1.01 g, 5.72 mmol) were added and the reaction mixture was heated to reflux at 100° C. The reaction course was followed by HPLC and determined to be complete after 1.25 hours. Silica gel was added and the solvent was removed under reduced pressure. The material was purified on silica gel using 5% ethyl acetate in hexanes as the eluent and was determined to be 85% pure by NMR (contained 10% starting material and 5% 5-bromo-2,2-dibromomethyl-benzoic acid methyl ester) and then used without further purification. 1H NMR (300.132 MHz, CDCl3) δ 8.10 (d, J=2.2 Hz, 1H), 7.62 (dd, J=8.3, 2.1 Hz, 1H), 7.34 (d, J=8.5 Hz, 1H), 4.90 (s, 2H), 4.90 (s, 3H).

Workup

  1. temperaturethe reaction mixture was heated
  2. additionSilica gel was added
  3. customthe solvent was removed under reduced pressure
  4. customThe material was purified on silica gel using 5% ethyl acetate in hexanes as the eluent
  5. customused without further purification

Sources & evidence

ORD record
ord-d587078cc49647c0b401dcc940a3b844
Source dataset
uspto-grants-2009_07
Patent number
US07566727B2

Linked notes

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