Hydrogen Bromide → biphenyl-4,4'-diylbis(phosphonic acid)

HRID 374236Notes

Reaction equation

HRID 374236 reaction equation
Br.C([O:4][P:5]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([P:22]([O:27]CC)(=[O:26])[O:23]CC)=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)(=[O:9])[O:6]CC)C.O>C(O)(=O)C>[C:16]1([C:13]2[CH:14]=[CH:15][C:10]([P:5]([OH:6])(=[O:4])[OH:9])=[CH:11][CH:12]=2)[CH:17]=[CH:18][C:19]([P:22]([OH:26])(=[O:23])[OH:27])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 53908436P,P,P′,P′-Tetraethyl P,P′-[1,1′-biphenyl]-4,4′-diylbis[phosphonate]

Product 1

HCID 279154biphenyl-4,4'-diylbis(phosphonic acid)Yield 66%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

66 ml of HBr at 33% by weight in acetic acid are added to 4.9 g (11.5 moles) of 4,4'-biphenyl-diphosphonic acid tetra-ethyl ester and the mixture is heated at 80° C. for 4 hours. After cooling to ambient temperature, 150 ml of H2O are added under agitation and the precipitate obtained is filtered, washed with water and vacuum dried (20 mm Hg) at 45° C. for one night. 2.29 g of 4,4'-biphenyl-diphosphonic acid, with a molar yield of 66% are obtained.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. customthe precipitate obtained
  3. filtrationis filtered
  4. washwashed with water and vacuum
  5. customdried (20 mm Hg) at 45° C. for one night

Sources & evidence

ORD record
ord-5e4f3f0dcfd24ea190ce2ec9da9b0d5c
Source dataset
uspto-grants-1992_11
Patent number
US05166380

Reaction notes

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