Phosphorus tribromide → HCID 57656575, compound

HRID 911445Notes

Reaction equation

HRID 911445 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-cc8b3b504e074e809a7dfdbff5b62830
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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