Phosphorus tribromide → 1016530-65-6

HRID 1878725Notes

Reaction equation

HRID 1878725 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:11])[N:6]([CH2:8][CH2:9]O)[CH:7]=1.P(Br)(Br)[Br:13]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:11])[N:6]([CH2:8][CH2:9][Br:13])[CH:7]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 434194335-bromo-1-(2-hydroxyethyl)pyridin-2(1H)-one

Product 1

HCID 246892801016530-65-6

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 5-bromo-1-(2-hydroxyethyl)pyridin-2(1 H)-one (460 mg, 2110 μmol) in CH2Cl2 (5 mL) at 0° C. under nitrogen was added phosphorous tribromide (595 μL, 6329 μmol). A precipitate formed at 0° C. The reaction mixture was heated at 40° C. for 3 days. The mixture was partitioned between CH2Cl2 and 5% NaHCO3 (vigorous gas evolution). The aqueous was extracted with CH2Cl2 (2×10 mL). The combined organics were dried over MgSO4, and concentrated to a white solid. MS (ESI pos. ion) m/z (MH+): 279/281/283. Calc'd exact mass for C7H7Br2NO: 278.

Workup

  1. customA precipitate formed at 0° C
  2. customThe mixture was partitioned between CH2Cl2 and 5% NaHCO3 (vigorous gas evolution)
  3. extractionThe aqueous was extracted with CH2Cl2 (2×10 mL)
  4. dry with materialThe combined organics were dried over MgSO4
  5. concentrationconcentrated to a white solid

Sources & evidence

ORD record
ord-b7108dabcc054546a4fc258ceaa0349d
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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