Toluene → HCID 68957047, compound

HRID 2191636Notes

Reaction equation

HRID 2191636 reaction equation
C1(C)C=CC=CC=1.Br[C:9]1[CH:21]=[CH:20][C:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[C:11]([N+:22]([O-:24])=[O:23])[CH:10]=1.[C:25](=[O:47])([O:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH:33]=1)[O:26][C:27]([CH3:30])([CH3:29])[CH3:28].C(=O)([O-])O.[Na+]>O.C(OCC)(=O)C.C(O)C>[C:27]([O:26][C:25]([O:31][C:32]1[CH:33]=[C:34]([C:9]2[CH:21]=[CH:20][C:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[C:11]([N+:22]([O-:24])=[O:23])[CH:10]=2)[CH:35]=[CH:36][CH:37]=1)=[O:47])([CH3:30])([CH3:28])[CH3:29]

Participants

8

Reactant 4

HCID 1140TolueneHCID 516892Sodium BicarbonateHCID 27739553-(tert-Butoxycarbonyloxy)phenylboronic acid pinacol esterHCID 26369829tert-Butyl 4-bromo-2-nitrobenzoate

Product 1

HCID 68957047HCID 68957047, compoundYield 87.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To toluene 24 mL solution of tert-butyl 4-bromo-2-nitrobenzoate 3.0 g were added ethanol 9.0 mL, water 4.5 mL, tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl carbonate 3.8 g, sodium hydrogen carbonate 2.1 g and tetrakis (triphenylphosphine)palladium(0) 0.57 g sequentially, and it was heated and refluxed under nitrogen atmosphere for 6 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and water were added to it. After insoluble matter was filtrated, the organic layer was separated and collected,dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Fuji SILYSIA Chemical Ltd., PSQ100B(spherical type), eluent; hexane:ethyl acetate=3:1] to give tert-butyl 4-(3-(tert-butoxycarbonyl)oxyphenyl)-2-nitrobenzoate 3.6 g of yellow oil.

Workup

  1. temperatureit was heated
  2. temperaturerefluxed under nitrogen atmosphere for 6 hours
  3. filtrationAfter insoluble matter was filtrated
  4. customthe organic layer was separated
  5. washafter washing with saturated sodium chloride aqueous solution
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-65915fe6e6304aeea56777715bbbc788
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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