Potassium Bromide → HCID 10221166, compound

HRID 1743019Notes

Reaction equation

HRID 1743019 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH2:14][P:15]([O:20]CC)([O:17]CC)=[O:16])=[CH:7][C:8]([O:12]C)=[N:9]2)=[CH:4][CH:3]=1.[K+].[Br-]>C[Si](Br)(C)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH2:14][P:15]([OH:17])([OH:20])=[O:16])=[CH:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 253877Potassium BromideHCID 22414268HCID 22414268, compound

Product 1

HCID 10221166HCID 10221166, compound

Reagents, catalysts & solvents 1

HCID 76113BromotrimethylsilaneSolvent

Procedure

A solution of diethylphosphonate 17 (160 mg; 0.57 mmol) in trimethylsilylbromide (4 ml) was refluxed overnight. The solvent/reagent was removed in vacuo and the residue was dissolved in 3 ml of 1N NaOH and washed with 2×1 ml of ether. The aqueous layer was acidified to pH 1 with 6N HCl and the precipitate which was formed was collected and washed with cold water, methanol and ether. The product was obtained as a white solid, mp 186° C. (dec) (80 mg; 60%). 1H NMR (D20): δ 3.06 (d, 2H, J=20.3 Hz); 6.54 (d, 1H, J=3.32 Hz); 7.12 (dd, 1H, J=2.03, 8.89 Hz); 7.36 (d, 1H, J=2.03 Hz); 7.89 (d, 1H, j=8.80 Hz). IR (KBr): 2931, 2828, 2360, 2309, 1658, 1643, 1532, 1406, 1224, 1147, 1093 cm-1. Anal. Calc' d for C10H9NO4ClP: C, 43.89; H, 3.32; N, 5.12. Found: C, 43.69; H, 3.41; N, 5.02.

Workup

  1. customThe solvent/reagent was removed in vacuo
  2. dissolutionthe residue was dissolved in 3 ml of 1N NaOH
  3. washwashed with 2×1 ml of ether
  4. customthe precipitate which was formed
  5. customwas collected
  6. washwashed with cold water, methanol and ether
  7. customThe product was obtained as a white solid, mp 186° C. (dec) (80 mg; 60%)

Sources & evidence

ORD record
ord-e4ec9653da54439784f91b1b1fdbe001
Source dataset
uspto-grants-1994_08
Patent number
US05342946

Reaction notes

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