Benzyl Bromide → HCID 53971539, compound

HRID 1018680Notes

Reaction equation

HRID 1018680 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-f7d54a6bcdcb4e57bc7fcfe50394a045
Source dataset
uspto-grants-2002_11
Patent number
US06482852B2

Reaction notes

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