Phosphorus tribromide → HCID 58372748, compound

HRID 888469Notes

Reaction equation

HRID 888469 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:16]=2[CH2:24]O)[CH:7]=1)[CH3:2].P(Br)(Br)[Br:28]>COCCOC>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:16]=2[CH2:24][Br:28])[CH:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 58372800HCID 58372800, compound

Product 1

HCID 58372748HCID 58372748, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of [3-(2-hydroxymethyl-4-nitro-phenoxy)-4-methoxy-phenyl]-acetic acid ethyl ester (15.14 g, 41.9 mmol) in DME was added phosphorus tribromide (5.92 mL, 62.8 mmol), and the reaction was stirred at room temperature overnight. After cooling to 0° C., the mixture was quenched with saturated aqueous NaHCO3 and extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated to give the title compound.

Workup

  1. temperatureAfter cooling to 0° C.
  2. customthe mixture 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

Sources & evidence

ORD record
ord-526da1c4a075466fadbe54bbc06d7561
Source dataset
uspto-grants-2012_08
Patent number
US08247602B2

Reaction notes

Loading…