Toluene → HCID 68962230, compound

HRID 2191619Notes

Reaction equation

HRID 2191619 reaction equation
[C:1]1(C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=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.C1(B(O)O)C=CC=CC=1.C(=O)([O-])O.[Na+]>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(O)C>[N+:22]([C:11]1[CH:10]=[C:9]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:21]=[CH:20][C:12]=1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])([O-:24])=[O:23]

Participants

8

Reactant 4

HCID 1140TolueneHCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 26369829tert-Butyl 4-bromo-2-nitrobenzoate

Product 1

HCID 68962230HCID 68962230, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To toluene 70 mL solution of tert-butyl 4-bromo-2-nitrobenzoate 8.8 g were added phenylboronic acid 4.3 g, sodium hydrogen carbonate 6.1 g, ethanol 26 mL, water 13 mL and tetrakis(triphenylphosphine)palladium (0) 1.7 g at room temperature sequentially, and it was heated and refluxed for 3 hours. After the reaction mixture was cooled to room temperature, water was added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after sequential washing with saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. Hexane was added to the obtained residue, solid matter was filtrated to give tert-butyl 2-nitro-4-phenylbenzoate 7.8 g of white solid.

Workup

  1. temperatureit was heated
  2. temperaturerefluxed for 3 hours
  3. customThe organic layer was separated
  4. washafter sequential washing with saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution
  5. customthe solvent was removed under reduced pressure
  6. additionHexane was added to the obtained residue, solid matter
  7. filtrationwas filtrated

Sources & evidence

ORD record
ord-1860ad31c18b4667a53f6fef1b6e3f4e
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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