Ammonium Chloride → (3-Bromo-6-chloropyridin-2-yl)(4-chlorophenyl)methanone

HRID 2401410Notes

Reaction equation

HRID 2401410 reaction equation
[Br:1][C:2]1[C:3]([C:9](N(OC)C)=[O:10])=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([Mg]Br)=[CH:18][CH:17]=1.[Cl-].[NH4+]>C1COCC1>[Br:1][C:2]1[C:3]([C:9]([C:19]2[CH:20]=[CH:21][C:16]([Cl:15])=[CH:17][CH:18]=2)=[O:10])=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 866667253-Bromo-6-chloro-N-methoxy-N-methylpicolinamideHCID 178478191HCID 178478191, compound

Product 1

HCID 86666726(3-Bromo-6-chloropyridin-2-yl)(4-chlorophenyl)methanoneYield 94.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromo-6-chloro-N-methoxy-N-methylpicolinamide (5.34 g, 19.1 mmol) in anhydrous THF (38 mL) at 0° C. was slowly added a solution of (4-chlorophenyl)magnesium bromide (1M in Et2O) (76 mL, 76 mmol). After 3 h at 0° C., a saturated aqueous solution of ammonium chloride was added and the product was extracted with MTBE (repeated 4 times). The organic layers were combined, dried over Na2SO4 and concentrated to dryness. The residue was purified by flash chromatography (hexane/EtOAc 10:0 to 8:2) to give the title compound as a white solid (5.98 g). LC/MS m/z 332 [M+H]+.

Workup

  1. extractionthe product was extracted with MTBE (repeated 4 times)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated to dryness
  4. customThe residue was purified by flash chromatography (hexane/EtOAc 10:0 to 8:2)

Sources & evidence

ORD record
ord-914340ec06b944d5bb312026ea8d90f2
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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