Benzene → Methyl 5-(2-(bromomethyl)-5-chlorophenyl)picolinate

HRID 405138

Reaction equation

HRID 405138 reaction equation
C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C1C=CC=CC=1.[Cl:25][C:26]1[CH:27]=[CH:28][C:29]([CH3:42])=[C:30]([C:32]2[CH:33]=[CH:34][C:35]([C:38]([O:40][CH3:41])=[O:39])=[N:36][CH:37]=2)[CH:31]=1.C1C(=O)N([Br:50])C(=O)C1>CCOC(C)=O>[Br:50][CH2:42][C:29]1[CH:28]=[CH:27][C:26]([Cl:25])=[CH:31][C:30]=1[C:32]1[CH:33]=[CH:34][C:35]([C:38]([O:40][CH3:41])=[O:39])=[N:36][CH:37]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 71060066Methyl 5-(5-chloro-2-methylphenyl)picolinate

Product 1

HCID 86674247Methyl 5-(2-(bromomethyl)-5-chlorophenyl)picolinate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Solid benzoyl peroxide (496 mg, 2.0 mmol) was added to a benzene solution (50 mL) of methyl 5-(5-chloro-2-methylphenyl)picolinate (3.6 g, 13.6 mmol) and NBS (2.7 g, 15.0 mmol) and the resulting mixture was refluxed. After 16 h the resulting mixture was cooled, diluted with EtOAc, washed with water and brine, dried (Na2SO4), and dry packed onto silica gel. Column chromatography yielded the title compound.

Workup

  1. temperaturethe resulting mixture was refluxed
  2. temperatureAfter 16 h the resulting mixture was cooled
  3. washwashed with water and brine
  4. dry with materialdried (Na2SO4)
  5. customdry

Sources & evidence

ORD record
ord-57635edebc2548bf9ce2ecd6a317cc89
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Linked notes

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