Potassium Phosphate, Tribasic → HCID 68459588, compound

HRID 502450Notes

Reaction equation

HRID 502450 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8](OS(C(F)(F)F)(=O)=O)[CH:7]=[C:6]([O:18][CH3:19])[CH:5]=1.[CH:21]1(B(O)O)[CH2:23][CH2:22]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>CC([O-])=O.CC([O-])=O.[Pd+2].O.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:5]=[C:6]([O:18][CH3:19])[CH:7]=[C:8]([CH:21]2[CH2:23][CH2:22]2)[CH:9]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 54576351HCID 54576351, compound

Product 1

HCID 68459588HCID 68459588, compoundYield 96.5%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

The above prepared 3-methoxy-5-trifluoromethanesulfonyloxy-benzoic acid methyl ester (0.350 g, 1.11 mmol) was dissolved under Ar in 4.5 ml of abs. toluene and 0.49 ml of water and treated successively with cyclopropyl boronic acid (0.191 g, 2 eq.), K3PO4 (1.272 g, 5.4 eq.), tricyclohexylphosphine (0.069 g, 0.22 eq.), and finally Pd(OAc)2 (0.028 g, 0.11 eq.). The reaction flask was closed with a septum and the mixture was allowed to react for 16 h at 100° C. Pouring onto crashed ice/NH4Cl, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (silica gel, hexane/AcOEt=9/1), afforded 0.221 g of the title compound as yellow oil, 97% pure according to GC-analysis.

Workup

  1. dissolutionwas dissolved under Ar in 4.5 ml of abs
  2. customThe reaction flask was closed with a septum
  3. customto react for 16 h at 100° C
  4. additionPouring
  5. extractionice/NH4Cl, twofold extraction with AcOEt
  6. washwashing with water
  7. dry with materialdrying over sodium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-dd7fd60ce4eb4572949635ddbf83f9d6
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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