Phosphorus oxybromide → HCID 67368349, compound

HRID 1676166Notes

Reaction equation

HRID 1676166 reaction equation
O[C:2]1[CH:7]=[CH:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[C:4](=[O:18])[CH:3]=1.P(Br)(Br)([Br:21])=O.C([O-])(O)=O.[Na+]>>[Br:21][C:2]1[CH:7]=[CH:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[C:4](=[O:18])[CH:3]=1

Participants

4

Reactant 3

HCID 24613Phosphorus oxybromideHCID 516892Sodium BicarbonateHCID 67072607HCID 67072607, compound

Product 1

HCID 67368349HCID 67368349, compoundYield 46.2%

Conditions

Temperature
100 °C

Procedure

A mixture of 4-hydroxy-1-(4-(methylsulfonyl)phenyl)pyridin-2(1H)-one (106.1 mg, 0.4 mmol) and phosphorous oxybromide (573.4 mg, 2.0 mmol, Alfa Aesar) was heated at 100° C. for 45 min and then cooed to room temperature. To the above residue was added saturated NaHCO3 aqueous solution at 0° C. followed by extraction with CH2Cl2 (3×). The combined extracts were washed with saturated NaHCO3 aqueous solution and brine, dried Na2SO4) and evaporated. The residual was purified by flash chromatography (0 to 100% EtOAc/hexanes) to yield 60.7 mg (46%) of the product as a yellow solid. MS (ESI) 328 (M+H).

Workup

  1. customcooed to room temperature
  2. extractionfollowed by extraction with CH2Cl2 (3×)
  3. washThe combined extracts were washed with saturated NaHCO3 aqueous solution and brine, dried Na2SO4) and
  4. customevaporated
  5. customThe residual was purified by flash chromatography (0 to 100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-f8e233fdc406446187fc3837f7abb7a7
Source dataset
uspto-grants-2011_08
Patent number
US08003796B2

Reaction notes

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