Potassium Phosphate, Tribasic → HCID 68458497, compound

HRID 502408Notes

Reaction equation

HRID 502408 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8](I)=[C:7]([O:12][CH2:13][CH3:14])[CH:6]=1)[CH3:2].[F:16][C:17]([F:28])([F:27])[C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C>[CH2:1]([O:3][C:4]([C:5]1[CH:10]=[CH:9][C:8]([C:21]2[CH:22]=[CH:23][C:18]([C:17]([F:28])([F:27])[F:16])=[CH:19][CH:20]=2)=[C:7]([O:12][CH2:13][CH3:14])[CH:6]=1)=[O:15])[CH3:2]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 23090718Ethyl 3-ethoxy-4-iodobenzoate

Product 1

HCID 68458497HCID 68458497, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

3-Ethoxy-4-iodo-benzoic acid ethyl ester (0.500 g, 1.56 mmol, CAS No. 741699-04-7) was dissolved under Ar in 12 ml of abs. DMF and treated successively with 4-(trifluoromethyl)phenyl boronic acid (0.356 g, 1.2 eq.), K3PO4 (0.564 g, 1.7 eq.), and Pd(PPh3)4 (0.054 g, 0.03 eq.). The mixture was allowed to react for 16 h at 80° C. Pouring onto crashed ice/NH4Cl, twofold extraction with AcOEt, washing with brine, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (silica gel, hexane/AcOEt=95/5) afforded finally 0.515 g of the title compound as white solid.

Workup

  1. customto react for 16 h at 80° C
  2. additionPouring
  3. extractionice/NH4Cl, twofold extraction with AcOEt
  4. washwashing with brine
  5. dry with materialdrying over sodium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-d01a313696e447fc99bac44219830ef1
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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