Potassium Phosphate, Tribasic → HCID 68507568, compound

HRID 1715152Notes

Reaction equation

HRID 1715152 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]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:5]1[CH:10]=[CH:9][C:8]([C:20]2[CH:21]=[CH:22][C:17]([F:16])=[CH:18][CH:19]=2)=[C:7]([O:12][CH2:13][CH3:14])[CH:6]=1)=[O:15])[CH3:2]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2856454-Fluorophenylboronic acidHCID 23090718Ethyl 3-ethoxy-4-iodobenzoate

Product 1

HCID 68507568HCID 68507568, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-ethoxy-4-iodo-benzoic acid ethyl ester (0.76 g, 2.37 mmol, 1.0 equiv; [CAS RN 741699-04-7]) in anhydrous DMF (12 mL) under Ar was added 4-fluorophenyl boronic acid (0.40 g, 2.86 mmol, 1.20 equiv), K3PO4 (0.86 g, 4.04 mmol, 1.70 equiv) and tetrakis(triphenylphosphine) palladium(0) (0.082 g, 0.071 mmol, 0.03 equiv) and the reaction mixture heated to 80° C. After 16 h, the reaction mixture was poured on crashed ice/NH4Cl, extracted twice with ethyl acetate, the combined organic phases washed with water and a sat. solution of NaCl, dried over MgSO4 and concentrated by evaporation under reduced pressure. The crude material was purified with silica column chromatography eluting with hexane/ethyl acetate (95:5) to yield 0.51 g (75%) of the title compound as a colorless oil. MS (ISP): 289.3 [M+H]+.

Workup

  1. additionthe reaction mixture was poured
  2. extractionextracted twice with ethyl acetate
  3. washthe combined organic phases washed with water
  4. dry with materiala sat. solution of NaCl, dried over MgSO4
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customThe crude material was purified with silica column chromatography
  7. washeluting with hexane/ethyl acetate (95:5)

Sources & evidence

ORD record
ord-4ef4acdfdd1d4818ab564ea496c9ba97
Source dataset
uspto-grants-2010_09
Patent number
US07799806B2

Reaction notes

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