Hydrochloric Acid → HCID 54249029, compound

HRID 1018679Notes

Reaction equation

HRID 1018679 reaction equation
[CH2:1]([O:3][P:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[I-:16].[Na+].CC1C=CC(S([N-]Cl)(=O)=O)=CC=1.O.O.O.[Na+].Cl>CN(C=O)C.O>[CH2:6]([O:5][P:4]([C:9]1[CH:14]=[C:13]([I:16])[CH:12]=[CH:11][C:10]=1[OH:15])(=[O:8])[O:3][CH2:1][CH3:2])[CH3:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 517414chloramine-T trihydrateHCID 2063513Diethyl (2-hydroxyphenyl)phosphonate

Product 1

HCID 54249029HCID 54249029, compoundYield 73.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a cooled (0° C.) mixture of (2-hydroxy-phenyl)-phosphonic acid diethyl ester (13.1 g, 56.9 mmol) and sodium iodide (10.2 g, 68.3 mmol) in DMF (200 mL) was added chloramine-T trihydrate (19.2 g, 68.3 mmol) over 5 min. After 10 min, the reaction was allowed to warm to rt and the mixture was allowed to stir at rt for 2 h. The mixture was diluted with H2O (50 mL), acidified using 0.5 N HCl and extracted twice with EtOAc. The organic extracts were pooled and washed sequentially with satd. Na2S2O3/brine (1/1) and then brine. The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was chromatographed over silica gel (elution with a stepwise gradient 5-15% EtOAc-hexanes) to give 14.9 g (73%) of a colorless solid after recrystallization (EtOAc-hexanes). Rf 0.30 (20% EtOAc-hexanes). Electrospray Mass Spectrum (50/50 acetonitrile/water) m/z 357 (M+H).

Workup

  1. temperatureTo a cooled
  2. extractionextracted twice with EtOAc
  3. washwashed sequentially with satd
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed over silica gel (
  7. washelution with a stepwise gradient 5-15% EtOAc-hexanes)

Sources & evidence

ORD record
ord-824b1f0677a14d7982eb83db8c4ee2d4
Source dataset
uspto-grants-2002_11
Patent number
US06482852B2

Reaction notes

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