Phosphorus oxychloride → 3-(3-Bromo-5-chlorophenoxy)-2-chloro-4-methylpyridine

HRID 505566Notes

Reaction equation

HRID 505566 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([Cl:17])[CH:16]=1)[O:5][C:6]1[C:7](O)=[N:8][CH:9]=[CH:10][C:11]=1[CH3:12].P(Cl)(Cl)([Cl:20])=O>>[Br:1][C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([Cl:17])[CH:16]=1)[O:5][C:6]1[C:7]([Cl:20])=[N:8][CH:9]=[CH:10][C:11]=1[CH3:12]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178428607HCID 178428607, compound

Product 1

HCID 866244793-(3-Bromo-5-chlorophenoxy)-2-chloro-4-methylpyridine

Conditions

Temperature
100 °C

Procedure

A suspension of 3-(3-bromo-5-chlorophenoxy)-4-methylpyridin-2-ol (340 mg, 1.081 mmol) in phosphorus oxychloride (10 mL, 107 mmol) was heated at 100° C. for 24 hours, after which the solvent was removed in vacuo. The resulting oil was quenched with saturated aqueous NaHCO3 (50 mL) and extracted with EtOAc (100 mL). The organic extract was washed with water (20 mL), dried over MgSO4, filtered, and the solvent removed on a rotary evaporator. This residue was purified using Waters PrepPak and eluting with a gradient of 5-95% ACN/H2O with 0.1% TFA. The desired fractions were combined and the solvent removed in vacuo to give the title compound. LRMS (M+1)=333.8.

Workup

  1. customafter which the solvent was removed in vacuo
  2. customThe resulting oil was quenched with saturated aqueous NaHCO3 (50 mL)
  3. extractionextracted with EtOAc (100 mL)
  4. extractionThe organic extract
  5. washwas washed with water (20 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customthe solvent removed on a rotary evaporator
  9. customThis residue was purified
  10. washeluting with a gradient of 5-95% ACN/H2O with 0.1% TFA
  11. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-4d162c07a3da4082abd9365f6bd9a16b
Source dataset
uspto-grants-2010_08
Patent number
US07781454B2

Reaction notes

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