Water → HCID 18472577, compound

HRID 1388025Notes

Reaction equation

HRID 1388025 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=2[CH:16]=1.B([O-])([O-])O[C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].O>C(OCC)(=O)C.C1(C)C=CC=CC=1.C(O)C>[F:25][C:22]1[CH:23]=[CH:24][C:19]([C:2]2[CH:3]=[CH:4][C:5]3[O:11][CH2:10][CH2:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=3[CH:16]=2)=[CH:20][CH:21]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 22990005Methyl 7-bromo-2,3-dihydro-1-benzooxepine-4-carboxylateHCID 867561584-Fluorophenyl borate

Product 1

HCID 18472577HCID 18472577, compoundYield 59%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To methyl 7-bromo-2,3-dihydro-1-benzoxepine-4-carboxylate (500 mg) were added 4-fluorophenyl borate (272 mg), potassium carbonate (537 mg), water (1.5 ml), ethanol (1.5 ml) and toluene (15 ml). Under argon atmosphere, the mixture was stirred at room temperature for 1 hour, and to the mixture was added tetrakistriphenyl-phosphine palladium (61 mg, 3 mol %). Under argon atmosphere, the mixture was refluxed for 21 hours, and to the mixture was added ethyl acetate (100 ml). The mixture was washed with water (50 ml) and saturated brine (50 ml), and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was removed, and the residue was purified with silica gel column chromatography to give methyl 7-(4-fluoro-phenyl)-2,3-dihydro-1-benzoxepine-4-carboxylate (310 mg, 59%) as pale yellow crystals.

Workup

  1. temperatureUnder argon atmosphere, the mixture was refluxed for 21 hours
  2. washThe mixture was washed with water (50 ml) and saturated brine (50 ml)
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customUnder reduced pressure, the solvent was removed
  5. customthe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-8906459be71a47b491a1cf90843eb727
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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