Phosphorus tribromide → HCID 57656575, compound

HRID 2041326Notes

Reaction equation

HRID 2041326 reaction equation
P(Br)(Br)[Br:2].O[CH2:6][C:7]1[CH:20]=[CH:19][C:10]([O:11][CH2:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:9][CH:8]=1>C1COCC1.CCOC(C)=O>[Br:2][CH2:6][C:7]1[CH:20]=[CH:19][C:10]([O:11][CH2:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 57655910HCID 57655910, compound

Product 1

HCID 57656575HCID 57656575, compoundYield 83.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Add phosphorous tribromide (1.45 g, 5.34 mmol) slowly to a solution of 1-(4-hydroxymethyl-phenoxy)-3,3-dimethylbutan-2-one (1.08 g, 4.85 mmol) in anhydrous THF under nitrogen at 0° C. Stir at 0° C. for 1 h and then raise to ambient temperature. Stir overnight. Dilute with EtOAc, wash with saturated aqueous NaHCO3, brine, dry over Na2SO4, filter and concentrate. Purify the residue by chromatography on silica gel eluting with EtOAc:hexane (1:6) to provide the title compound (1.152 g, 83%). MS (ES+) m/z: 205 (M-Br)+.

Workup

  1. temperatureraise to ambient temperature
  2. stirringStir overnight
  3. washwash with saturated aqueous NaHCO3, brine
  4. dry with materialdry over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the residue by chromatography on silica gel eluting with EtOAc:hexane (1:6)

Sources & evidence

ORD record
ord-059b6c174f0f497eb6b30a101d35aff6
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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