Benzoyl Peroxide → Methyl 3-bromo-2-(bromomethyl)benzoate

HRID 552390Notes

Reaction equation

HRID 552390 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Br:10])[C:5]=1[CH3:11].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:31]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Br:10])[C:5]=1[CH2:11][Br:31]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 12929135Methyl 3-Bromo-2-methylbenzoate

Product 1

HCID 21907554Methyl 3-bromo-2-(bromomethyl)benzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
90 °C

Procedure

3-Bromo-2-methyl-benzoic acid methyl ester (2.0 g, 8.73 mmol) is dissolved in carbon tetrachloride (35 mL). The solution is kept under an inert atmosphere by bubbling nitrogen through the mixture while benzoyl peroxide (106 mg, 0.44 mmol) and N-bromosuccinimide (1.55 g, 8.73 mmol) are added. The mixture is purged with vacuum and nitrogen, and is then refluxed at 90° C. for 2 hours. The reaction mixture is cooled to 0° C. and filtered. The filtrate is evaporated to yield the title compound, which is used as such for the next step.

Workup

  1. additionare added
  2. customThe mixture is purged with vacuum and nitrogen
  3. temperatureThe reaction mixture is cooled to 0° C.
  4. filtrationfiltered
  5. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-67cd96f4bcf04b1294e43a0f81c3f9c1
Source dataset
uspto-grants-2011_05
Patent number
US07951818B2

Reaction notes

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