Potassium Phosphate, Tribasic → HCID 23157405, compound

HRID 507948Notes

Reaction equation

HRID 507948 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17](O)[CH:18]=1)[C:12]([O:14][CH3:15])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)C(C)C)C.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[CH3:44][C:45]1[CH:50]=[CH:49][CH:48]=[C:47]([CH3:51])[C:46]=1B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>ClCCl.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>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:12]([O:14][CH3:15])=[O:13])[CH:16]=[C:17]([C:46]2[C:47]([CH3:51])=[CH:48][CH:49]=[CH:50][C:45]=2[CH3:44])[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 62657Potassium Phosphate, TribasicHCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 5833222,6-Dimethylphenylboronic acidHCID 7472028Methyl 3-(benzyloxy)-5-hydroxybenzoate

Product 1

HCID 23157405HCID 23157405, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 3-(benzyloxy)-5-hydroxybenzoate (3.10 g, 12.0 mmol) and N-ethyldiisopropylamine (2.51 mL, 14.4 mmol) in dichloromethane (30 mL) was added dropwise trifluoromethanesulfonic anhydride (2.22 mL, 13.2 mmol) under ice-cooling, and the mixture was stirred at the same temperature for 1 hr. The reaction mixture was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was dissolved in 1,2-dimethoxyethane (40 mL), and 2,6-dimethylphenylboronic acid (2.25 g, 15.0 mmol), tripotassium phosphate (3.82 g, 18.0 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.693 g, 0.600 mmol) were added. The reaction mixture was stirred under an argon atmosphere at 80° C. for 15 hr. The reaction mixture was concentrated under reduced pressure, and water was added to the residue. The mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-20% ethyl acetate/hexane) to give the title compound (3.60 g, yield 87%) as a yellow oil.

Workup

  1. temperaturecooling
  2. washThe reaction mixture was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe obtained residue was dissolved in 1,2-dimethoxyethane (40 mL)
  6. stirringThe reaction mixture was stirred under an argon atmosphere at 80° C. for 15 hr
  7. concentrationThe reaction mixture was concentrated under reduced pressure, and water
  8. additionwas added to the residue
  9. extractionThe mixture was extracted with ethyl acetate
  10. washThe extract was washed with saturated brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customThe residue was purified by silica gel column chromatography (hexane-20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c115d94df71f4fd289670fffef256f43
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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