Benzoyl Peroxide → Methyl 2-(bromomethyl)-6-nitrobenzoate

HRID 859993

Reaction equation

HRID 859993 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1[CH3:13].[Br:15]NC(=O)CCC(N)=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:14])[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:13][Br:15]

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 596057Methyl 2-methyl-6-nitrobenzoateHCID 9834204N-Bromosuccinamide

Product 1

HCID 21708527Methyl 2-(bromomethyl)-6-nitrobenzoateYield 70%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Into a stirring solution of methyl-2-methyl-6-nitrobenzoate (3.9 g, 20 mmols) in 50 mL CCl4 anhydrous, N-bromosuccinamide (3.56 g, 20 mmols), and benzoylperoxide (25 mg, 0.10 mmols), was added. The reaction mixture was heated under reflux for about 24 hours. TLC developed in EtOAc/Hex 1:9 mixture showed formation of new product. The CCl4 was evaporated and on leaving a viscous product at RT, light yellow crystals of product were separated. The product was purified by flash silica gel column eluted with Hex/EtOAc. 9:1 mixture to give 3.0 g light yellow crystals (70%). A small portion of dibrominated product was also separated. 1H NMR in CDCl3 confirmed the product as methyl-2-bromomethyl-6-nitrobenzoate.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for about 24 hours
  3. customThe CCl4 was evaporated
  4. customon leaving a viscous product at RT
  5. customlight yellow crystals of product were separated
  6. customThe product was purified by flash silica gel column
  7. washeluted with Hex/EtOAc

Sources & evidence

ORD record
ord-aaf6c9905a744904ab15374aa21eafde
Source dataset
uspto-grants-2006_12
Patent number
US07153867B2

Linked notes

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