Benzyl Bromide → HCID 53971539, compound

HRID 1368346Notes

Reaction equation

HRID 1368346 reaction equation
[CH2:1]([O:3][P:4]([C:9]1[CH:14]=[C:13]([I:15])[CH:12]=[CH:11][C:10]=1[OH:16])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C>[CH2:1]([O:3][P:4]([C:9]1[CH:14]=[C:13]([I:15])[CH:12]=[CH:11][C:10]=1[O:16][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 54249029HCID 54249029, compound

Product 1

HCID 53971539HCID 53971539, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of (2-hydroxy-5-iodo-phenyl)-phosphonic acid diethyl ester (14.7 g, 41.2 mmol) and cesium carbonate, (17.4 g, 53.5 mmol) in DMF (150 mL) was added benzyl bromide (6.40 mL, 54 mmol). The reaction was allowed to stir for 2.5 days at rt at which point the reaction was concentrated under reduced pressure, the residue diluted in 0.5 N HCl (30 mL) and extracted twice with EtOAc. The pooled organic extracts were washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to give 17.4 g (91%) of a colorless solid after recrystallization (EtOAc-hexanes). Rf 0.36 (1:1 EtOAc-hexanes). Electrospray Mass Spectrum (50/50 acetonitrile/water) m/z 447 (M+H).

Workup

  1. concentrationwas concentrated under reduced pressure
  2. additionthe residue diluted in 0.5 N HCl (30 mL)
  3. extractionextracted twice with EtOAc
  4. washThe pooled organic extracts were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e67f53a970594a8fa8cd70dc9a9cc3ed
Source dataset
uspto-grants-2003_06
Patent number
US06573295B2

Reaction notes

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