Bromotrimethylsilane → METHYLPHENYLPHOSPHINIC ACID

HRID 1863196Notes

Reaction equation

HRID 1863196 reaction equation
C[Si](Br)(C)C.[CH3:6][P:7]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:17])[O:8]CCC1C=CC=CC=1>>[CH3:6][P:7]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:8])[OH:17]

Participants

3

Reactant 2

HCID 76113BromotrimethylsilaneHCID 86736644HCID 86736644, compound

Product 1

HCID 345468METHYLPHENYLPHOSPHINIC ACID

Procedure

Trimethylsilylbromide (15 ml., 0.1 mole) is added portionwise to methylphenyl phosphinic acid, phenethyl ester (15.2 g.,0.1 mole) at a rate to maintain reflux temperature. Following the addition, the mixture is stirred one hour at ambient temperature. The volatiles are removed in vacuo. The addition of water (10 ml.) to the liquid residue (20.6 g.) results in the separation of a white solid. The mixture is stirred at ambient temperature overnight, followed by filtration, with a recovery of 14 g. of solid. It is recrystallized from dichloromethane (80 ml.) to give methylphenylphosphinic acid, 9.9 g. (72%), m.p. 133°-135°.

Workup

  1. temperatureto maintain
  2. temperaturereflux temperature
  3. additionthe addition
  4. customThe volatiles are removed in vacuo
  5. additionThe addition of water (10 ml.) to the liquid residue (20.6 g.)
  6. customresults in the separation of a white solid
  7. stirringThe mixture is stirred at ambient temperature overnight
  8. filtrationfollowed by filtration, with a recovery of 14 g
  9. customIt is recrystallized from dichloromethane (80 ml.)

Sources & evidence

ORD record
ord-4650afab87024b47ad22984617ce22c4
Source dataset
uspto-grants-1979_09
Patent number
US04168267

Reaction notes

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