Benzoyl Peroxide → HCID 57429424, compound

HRID 1640012Notes

Reaction equation

HRID 1640012 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:13])=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[Br:14]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[CH:3]=[CH:4][C:5]([CH2:13][Br:14])=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 25067287Ethyl 5-bromo-2-methylbenzoate

Product 1

HCID 57429424HCID 57429424, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of ethyl 5-bromo-2-methylbenzoate (7.52 g, 30.9 mmol), N-bromosuccinimide (6.05 g, 34.0 mmol) and benzoyl peroxide (0.75 g, 3.10 mmol) in carbon tetrachloride (150 ml) was heated to 70° C. in an oil bath for 18 h. After this time, the mixture was cooled to room temperature and the solids removed by filtration. The filtrate was then concentrated under reduced pressure and purified by flash chromatography (silica, gradient 1-10%, ethyl acetate/hexanes) afforded ethyl 5-bromo-2-(bromomethyl)benzoate (7.57 g, 76%) as a clear oil: 1H NMR (300 MHz, CDCl3) 8.09 (d, J=2.2 Hz, 1H), 7.61 (dd, J=8.3, 2.2 Hz, 1H), 7.33 (d, J=8.2 Hz, 1H), 4.90 (s, 2H), 4.42 (q, J=7.2 Hz, 2H), 1.43 (t, J=7.1 Hz, 3H).

Workup

  1. temperatureAfter this time, the mixture was cooled to room temperature
  2. customthe solids removed by filtration
  3. concentrationThe filtrate was then concentrated under reduced pressure
  4. custompurified by flash chromatography (silica, gradient 1-10%, ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-fb45852145d94e69910c1cfba60f9e0e
Source dataset
uspto-grants-2012_02
Patent number
US08110681B2

Reaction notes

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