Ethanol → HCID 58027130, compound

HRID 909288Notes

Reaction equation

HRID 909288 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1B(O)O.Br[C:14]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17].C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C1(C)C=CC=CC=1.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.O.C(OCC)(=O)C>[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[C:14]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17]

Participants

9

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 245494Methyl 2-Bromo-5-nitrobenzoateHCID 27832802,3,4-Trifluorobenzeneboronic acid

Product 1

HCID 58027130HCID 58027130, compoundYield 53%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 2,3,4-trifluorophenylboronic acid (4.70 g, 26.7 mmol), methyl 2-bromo-5-nitrobenzoate (9.02 g, 34.7 mmol), sodium carbonate (8.49 g, 80.1 mmol) and tetrakis(triphenylphosphine)palladium(0) (1.55 g, 1.34 mmol) was suspended in a mixture of toluene (160 mL)-ethanol (40 mL)-water (80 mL), and then the mixture was stirred under nitrogen atmosphere at 95° C. overnight. After cooling down, ethyl acetate (200 mL) and water (200 mL) were added thereto, and then separated. The organic layer was washed with saturated brine (150 mL), dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (4.37 g) as a brown oil. (Yield 53%)

Workup

  1. temperatureAfter cooling down
  2. customseparated
  3. washThe organic layer was washed with saturated brine (150 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-ce25cf8a27db4b459d3071d968b8fe97
Source dataset
uspto-grants-2011_09
Patent number
US08017775B2

Reaction notes

Loading…