Aniline → Aniline;2-bromoethylphosphonic acid

HRID 235709

Reaction equation

HRID 235709 reaction equation
C([O:3][P:4]([CH2:9][CH2:10][Br:11])(=[O:8])[O:5]CC)C.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>Br.C(O)C>[C:13]1([NH2:12])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Br:11][CH2:10][CH2:9][P:4](=[O:3])([OH:8])[OH:5]

Participants

5

Reactant 2

HCID 6115AnilineHCID 79218Diethyl (2-bromoethyl)phosphonate

Product 1

HCID 12601853Aniline;2-bromoethylphosphonic acidYield 53.2%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 702EthanolSolvent

Procedure

A solution of about 50 g of diethyl-2-bromoethyl-phosphonate in about 255 ml of about 48% hydrobromic acid was kept at reflux (about 95°-100° C.) overnight. The solvent was removed under reduced pressure and the residue evaporated twice with toluene, giving a syrup. This syrup was dissolved in about 65 ml of about 99% ethanol, about 20 g of aniline was added dropwise and the solid was collected, washed with cold about 99% ethanol (at about 0° C.) and dried in vacuo, giving about 30.6 g of the desired reagent, mp 157°-158° C.

Workup

  1. temperatureat reflux (about 95°-100° C.) overnight
  2. customThe solvent was removed under reduced pressure
  3. customthe residue evaporated twice with toluene
  4. customgiving a syrup
  5. customthe solid was collected
  6. washwashed with cold about 99% ethanol (at about 0° C.)
  7. customdried in vacuo

Sources & evidence

ORD record
ord-5d1e1bdf5d674b32b63e5a0ec0e63fca
Source dataset
uspto-grants-1987_02
Patent number
US04640913

Linked notes

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