Phosphorus tribromide → HCID 58237612, compound

HRID 885260Notes

Reaction equation

HRID 885260 reaction equation
O[CH2:2][C:3]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:4]=1[O:5][C:6]1[CH:7]=[C:8]([CH:12]([CH3:16])[C:13]([OH:15])=[O:14])[CH:9]=[CH:10][CH:11]=1.P(Br)(Br)[Br:26]>COCCOC>[Br:26][CH2:2][C:3]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:4]=1[O:5][C:6]1[CH:7]=[C:8]([CH:12]([CH3:16])[C:13]([OH:15])=[O:14])[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 58237556HCID 58237556, compound

Product 1

HCID 58237612HCID 58237612, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To 2-[3-(2-hydroxymethyl-4-trifluoromethyl-phenoxy)-phenyl]-propionic acid (˜0.30 mmol) in DME (5 mL) was added phosphorus tribromide (0.06 mL, 0.60 mmol), and the solution was stirred at room temperature for 3 hours. After cooling to 0° C., the reaction was quenched with saturated aqueous NaHCO3 and extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was purified by silica gel chromatography to give the desired product.

Workup

  1. temperatureAfter cooling to 0° C.
  2. customthe reaction was quenched with saturated aqueous NaHCO3
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-71b46a53f83f4a1bac7e5de91dbacde2
Source dataset
uspto-grants-2012_08
Patent number
US08242145B2

Reaction notes

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