Bromotrimethylsilane → Phosphonic acid, P-(3-aminophenyl)-

HRID 705452

Reaction equation

HRID 705452 reaction equation
C[Si](Br)(C)C.C[O:7][P:8]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-])=O)[CH:12]=1)(=[O:10])[O-:9]>CN(C=O)C>[NH2:17][C:13]1[CH:12]=[C:11]([P:8](=[O:7])([OH:10])[OH:9])[CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 117629312HCID 117629312, compound

Product 1

HCID 79477Phosphonic acid, P-(3-aminophenyl)-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

4 mL of DMF and trimethylsilyl bromide (1 mL) were added to the mixture (170 mg) of monomethyl(3-nitrophenyl)phosphonate and dimethyl ester, and stirred at 60° C. for 2 hours. After removing a solvent, the mixture was dissolved in a mixed solvent of water and methanol. Pd/C in catalyst quantity was added thereto and stirred under hydrogen atmosphere overnight. After filtering out the catalyst, a solvent was removed to obtain a crude product of (3-aminophenyl)phosphonic acid.

Workup

  1. customAfter removing a solvent
  2. dissolutionthe mixture was dissolved in a mixed solvent of water and methanol
  3. additionPd/C in catalyst quantity was added
  4. stirringstirred under hydrogen atmosphere overnight
  5. filtrationAfter filtering out the catalyst
  6. customa solvent was removed

Sources & evidence

ORD record
ord-6a63d25663584b4a98789a2ec6aac73f
Source dataset
uspto-grants-2015_11
Patent number
US09174932B2

Linked notes

Loading…