Triethylamine → Methyl 2-(diphenylphosphanyl)benzoate

HRID 430045Notes

Reaction equation

HRID 430045 reaction equation
[C:1]1([PH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)S(O[C:20]1[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=1[C:22]([O:24][CH3:25])=[O:23])(=O)=O.C(N(CC)CC)C>CC#N.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:8]1([P:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:20]2[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=2[C:22]([O:24][CH3:25])=[O:23])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 70017DiphenylphosphineHCID 11011497methyl 2-trifluoromethanesulfonyloxybenzoate

Product 1

HCID 13741333Methyl 2-(diphenylphosphanyl)benzoate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

Diphenylphosphine (0.94 mL, 5.40 mmol, 1 eq) was added to a stirred solution of methyl 2-trifluoromethanesulfonyloxybenzoate (1.531 g, 5.39 mmol, 1 eq), triethylamine (0.85 mL, 6.1 mmol, 1.1 eq) and palladium acetate (0.005 g, 0.02 mmol, 0.004 eq) in degassed MeCN (10 mL) instantly giving a red coloration. The solution was heated at reflux under nitrogen for 17 hours. The blood-red solution was allowed to cool and an aliquot taken for NMR analysis.

Workup

  1. custominstantly giving a red coloration
  2. temperatureThe solution was heated
  3. temperatureat reflux under nitrogen for 17 hours
  4. temperatureto cool

Sources & evidence

ORD record
ord-afb70d1805d04f68b3f24cdd2830e2a3
Source dataset
uspto-grants-2001_11
Patent number
US06320068B1

Reaction notes

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