Potassium Phosphate, Tribasic → HCID 58575084, compound

HRID 1189467Notes

Reaction equation

HRID 1189467 reaction equation
Br[C:2]1[CH:11]=[C:10]([F:12])[C:9]([N+:13]([O-:15])=[O:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH:16]1(OB(O)O)[CH2:18][CH2:17]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C>[CH:16]1([C:2]2[CH:11]=[C:10]([F:12])[C:9]([N+:13]([O-:15])=[O:14])=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])[CH2:18][CH2:17]1

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 43449031Benzoic acid, 2-bromo-4-fluoro-5-nitro-, methyl esterHCID 66812283HCID 66812283, compound

Product 1

HCID 58575084HCID 58575084, compoundYield 62.2%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

Under a nitrogen atmosphere, to a mixed liquid of 2.58 g of methyl 2-bromo-4-fluoro-5-nitrobenzoate in 50 mL of toluene and 1 mL of water were added 956 mg of cyclopropylboric acid, 360 mg of tricyclohexyl phosphine, 3.95 g of tripotassium phosphate, and 140 mg of palladium acetate, followed by stirring at 110° C. for 1.5 hours. The mixture was poured into a mixed liquid of water and ethyl acetate, and the insoluble materials were removed by filtration. The aqueous layer was separated, the organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (normal hexane/ethyl acetate) to obtain 1.38 g of methyl 2-cyclopropyl-4-fluoro-5-nitrobenzoate.

Workup

  1. customthe insoluble materials were removed by filtration
  2. customThe aqueous layer was separated
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (normal hexane/ethyl acetate)

Sources & evidence

ORD record
ord-44d35c8e220942649d058357b343738f
Source dataset
uspto-grants-2014_03
Patent number
US08674096B2

Reaction notes

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