Ethanol → HCID 67341350, compound

HRID 1673518Notes

Reaction equation

HRID 1673518 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][C:3]=1[CH3:9].C(=O)([O-])O.[Na+].C(O)C.[C:18]([NH:26][C:27]1[CH:39]=[C:38](B2OC(C)(C)C(C)(C)O2)[CH:37]=[CH:36][C:28]=1[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=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.C1(C)C=CC=CC=1>[C:18]([NH:26][C:27]1[CH:39]=[C:38]([C:6]2[CH:5]=[CH:4][C:3]([CH3:9])=[C:2]([Cl:1])[CH:7]=2)[CH:37]=[CH:36][C:28]=1[C:29]([O:31][C:32]([CH3:34])([CH3:35])[CH3:33])=[O:30])(=[O:25])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

9

Reactant 4

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 28013292-Chloro-4-iodotolueneHCID 67342196HCID 67342196, compound

Product 1

HCID 67341350HCID 67341350, compound

Reagents, catalysts & solvents 4

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

Procedure

0.031 mL of 2-chloro-4-Iodotoluene, 39 mg of sodium hydrogen carbonate, 0.6 mL of ethanol, 0.3 mL of water and 11 mg of tetrakis(triphenylphosphine)palladium(0) were added to 1.6 mL of toluene solution containing 79 mg of tert-butyl 2-(benzamido)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate at room temperature, and the resulting mixture was heated to reflux for 8 hours. After the reaction mixture was cooled to room temperature, 11 mg of tetrakis(triphenylphosphine)palladium(9) was added and the resulting mixture was heated to reflux for 7 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and water were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; hexane:ethyl acetate=10:1] to obtain tert-butyl 2-(benzamido)-4-(3-chloro-4-methylphenyl)benzoate as white solid.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 8 hours
  3. temperaturethe resulting mixture was heated
  4. temperatureto reflux for 7 hours
  5. temperatureAfter the reaction mixture was cooled to room temperature
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous magnesium sulfate
  8. washafter washed with a saturated sodium chloride aqueous solution
  9. customthe solvent was evaporated under reduced pressure
  10. customThe obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; hexane:ethyl acetate=10:1]

Sources & evidence

ORD record
ord-4b3fd4ff2e9c4cd99b4834e9556a2390
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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