Ethanol → Tert-butyl 2-(benzamido)-4-(4-nitrophenyl)benzoate

HRID 1673454Notes

Reaction equation

HRID 1673454 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])O.[Na+].C(O)C.[C:21]([NH:29][C:30]1[CH:42]=[C:41](Br)[CH:40]=[CH:39][C:31]=1[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=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.C1(C)C=CC=CC=1.O>[C:21]([NH:29][C:30]1[CH:42]=[C:41]([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH:40]=[CH:39][C:31]=1[C:32]([O:34][C:35]([CH3:37])([CH3:38])[CH3:36])=[O:33])(=[O:28])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 516892Sodium Bicarbonate2×HCID 27735524-Nitrophenylboronic acidHCID 67343005Tert-butyl 2-(benzamido)-4-bromobenzoate

Product 1

HCID 67342488Tert-butyl 2-(benzamido)-4-(4-nitrophenyl)benzoateYield 18%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

0.11 g of 4-nitrophenylboronic acid, 0.11 g of sodium hydrogen carbonate, 1.2 mL of ethanol, 0.6 mL of water and 31 mg of tetrakis(triphenylphosphine)palladium(0) were added to 4.0 mL of toluene solution containing 0.20 g of tert-butyl 2-(benzamido)-4-bromobenzoate, and the resulting mixture was heated to reflux under nitrogen atmosphere for 3 hours. A saturated sodium hydrogen carbonate aqueous solution was added after the reaction mixture was cooled to room temperature. 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 40 mg of tert-butyl 2-(benzamido)-4-(4-nitrophenyl)benzoate as white solid.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux under nitrogen atmosphere for 3 hours
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. washafter washed with a saturated sodium chloride aqueous solution
  6. customthe solvent was evaporated under reduced pressure
  7. 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-3a7264cc5a4e449c92cdbb021ce58101
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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