Sodium Carbonate → HCID 22647396, compound

HRID 393757Notes

Reaction equation

HRID 393757 reaction equation
[Br:1][C:2]1[CH:15]=[C:14]([CH3:16])[C:5]([O:6][C:7]2[CH:12]=[CH:11][N+:10]([O-])=[CH:9][CH:8]=2)=[C:4]([CH3:17])[CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].O=P(Cl)(Cl)[Cl:26]>>[Br:1][C:2]1[CH:15]=[C:14]([CH3:16])[C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([Cl:26])[CH:8]=2)=[C:4]([CH3:17])[CH:3]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 22647401HCID 22647401, compound

Product 1

HCID 22647396HCID 22647396, compoundYield 73%

Conditions

Temperature
105 °C

Procedure

A suspension of 4-(4-Bromo-2,6-dimethyl-phenoxy)-pyridine 1-oxide (14, 10 g, 34 mmol, 1 equiv) and Na2CO3 (3.6 g, 34 mmol, 1 equiv) in POCl3 (100 mL) was heated to 105° C. for 30 h. The reaction was cooled to RT and the POCl3 was removed by rotary evaporation. The residue was dissolved in EtOAc and partioned into a chilled biphasic solution of EtOAc and 1 N NaOH. The aqueous layer was treated with NaOH (s) until the pH >1. The aqueous layer was extracted with EtOAc (3×), and the combined organics were washed with brine, dried (MgSO4) and concentrated. Recrystallization (EtOH) provided the desired material as off-white crystals (73%). 1H NMR (300 MHz, CDCl3) δ8.21 (d, J=6.2 Hz, 1H), 7.28 (s, 2H), 6.66 (m, 2H), 2.10 (s, 6H). 13C NMR (100 MHz, CDCl3) δ165.6, 153.5, 151.3, 149.0, 133.3, 132.5, 119.6, 110.7, 110.2, 16.4.

Workup

  1. temperatureThe reaction was cooled to RT
  2. customthe POCl3 was removed by rotary evaporation
  3. dissolutionThe residue was dissolved in EtOAc
  4. additionThe aqueous layer was treated with NaOH (s) until the pH >1
  5. extractionThe aqueous layer was extracted with EtOAc (3×)
  6. washthe combined organics were washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customRecrystallization (EtOH)

Sources & evidence

ORD record
ord-bb866467636b408d8212c5117d619d39
Source dataset
uspto-grants-2004_10
Patent number
US06809109B2

Reaction notes

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