1-Bromo-3-chlorobenzene → HCID 10869200, compound

HRID 368969Notes

Reaction equation

HRID 368969 reaction equation
[Mg].Br[C:3]1[CH:4]=[C:5]([Cl: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](O)=[O:14].[Cl-].[NH4+]>O1CCCC1>[Cl:10][C:11]1[C:12]([C:13](=[O:14])[C:3]2[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[CH:4]=2)=[CH:16][CH:17]=[C:18]([CH3:20])[N:19]=1

Participants

6

Reactant 4

HCID 79281-Bromo-3-chlorobenzeneHCID 25517Ammonium ChlorideHCID 1217242-Chloro-6-methylnicotinic acidHCID 5462224Magnesium

Product 1

HCID 10869200HCID 10869200, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Magnesium (4.8 g, 200 mmol) was added to a tetrahydrofuran (400 ml) solution of 3-bromochlorobenzene (38 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 (9.2 g, 53 mmol) and then stirred overnight 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 (chloroform) to give 2-chloro-3-(3-chlorobenzoyl)-6-methylpyridine (6.25 g, 44%) as an oily material.

Workup

  1. customSince spontaneous exothermic reaction
  2. temperatureThe reaction solution was cooled to -40° C.
  3. stirringstirred overnight 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 (chloroform)

Sources & evidence

ORD record
ord-4db5afa776854204a37080e4cd08ba4c
Source dataset
uspto-grants-2000_10
Patent number
US06136810

Reaction notes

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