Phosphorus tribromide → 4-broMo-5-Methoxy-2-Methylpyridine

HRID 2204332Notes

Reaction equation

HRID 2204332 reaction equation
[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][N+:5]([O-])=[C:4]([CH3:11])[CH:3]=1.P(Br)(Br)Br>C(Cl)(Cl)Cl.C(Cl)Cl>[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][N:5]=[C:4]([CH3:11])[CH:3]=1

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 86703139HCID 86703139, compound

Product 1

HCID 735548294-broMo-5-Methoxy-2-Methylpyridine

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-5-methoxy-2-methyl-pyridine 1-oxide (Step AL4) (150 mg, 0.7 mmol) in CHCl3 (2 mL) at 10° C. was added dropwise PBr3 (78 μL, 0.826 mmol). The mixture was stirred at rt for 4 h, then at 50° C. for 1 h. The reaction mixture was dissolved in CH2Cl2 and extracted with a saturated aqueous solution of NaHCO3, washed with brine, dried (Na2SO4), filtered and concentrated. The product was crystallised (CH2Cl2/TBME). ESI-MS: tR=0.69 min, [M+H]+ 202.0/204.0 (LC-MS 1).

Workup

  1. waitat 50° C. for 1 h
  2. extractionextracted with a saturated aqueous solution of NaHCO3
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe product was crystallised (CH2Cl2/TBME)

Sources & evidence

ORD record
ord-20be6cdbf5344d469023a46bad09fda7
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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