3-Bromotoluene → HCID 11053930, compound

HRID 368971Notes

Reaction equation

HRID 368971 reaction equation
[Mg].Br[C:3]1[CH:4]=[C:5]([CH3:9])[CH:6]=[CH:7][CH:8]=1.[Cl:10][C:11]1[N:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=O.[Cl-].[NH4+]>O1CCCC1>[Cl:10][C:11]1[C:12]([C:13](=[O:15])[C:3]2[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[CH:4]=2)=[CH:16][CH:17]=[C:18]([CH3:20])[N:19]=1

Participants

6

Reactant 4

HCID 115603-BromotolueneHCID 25517Ammonium ChlorideHCID 1217242-Chloro-6-methylnicotinic acidHCID 5462224Magnesium

Product 1

HCID 11053930HCID 11053930, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Magnesium (4.82 g, 200 mmol) was added to a tetrahydrofuran (300 ml) solution of 3-bromotoluene (35.1 g, 200 mmol), and the mixture was stirred at room temperature. Since spontaneous exothermic reaction occurred, the stirring was continued until the exothermicity was ceased. The reaction solution was cooled to -40° C., mixed with 2-chloro-6-methylnicotinic acid (11.6 g, 68 mmol) and then stirred for 16 hours at room temperature. The reaction solution was mixed with saturated ammonium chloride aqueous solution and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, magnesium sulfate was removed by filtration and then the filtrate was concentrated under a reduced pressure. Thereafter, the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 2-chloro-6-methyl-3-(3-methylbenzoyl)pyridine (8.70 g, 52%) as a pale yellow oily material.

Workup

  1. customSince spontaneous exothermic reaction
  2. temperatureThe reaction solution was cooled to -40° C.
  3. stirringstirred for 16 hours at room temperature
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate, magnesium sulfate
  6. customwas removed by filtration
  7. concentrationthe filtrate was concentrated under a reduced pressure
  8. customThereafter, the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-894023bd3d4e4540a4ee07cdb672db17
Source dataset
uspto-grants-2000_10
Patent number
US06136810

Reaction notes

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