Ethanol → 4-Nitro-1,1'-biphenyl

HRID 36721

Reaction equation

HRID 36721 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>COC(OC)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(C)=O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 114661-Bromo-4-nitrobenzeneHCID 66827Phenylboronic Acid

Product 1

HCID 71144-Nitro-1,1'-biphenylYield 127.3%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8857Ethyl AcetateSolventHCID 107951,1-DimethoxyethaneSolvent

Procedure

12.50 g (61.9 mmol) of 1-bromo-4-nitrobenzene were added to 358 mg, (310 μmol, 0.5 mole %) of tetrakis (triphenyl-phosphine) palladium in 200 ml of dimethoxy-ethane. After stirring for 10 minutes, 11.3 g (92.8 mmol) of phenylboronic acid and 100 ml of ethanol were added. After a further 10 minutes, 263 ml, (526 mmol, 8.5 equiv) of 2M aqueous sodium carbonate were added and the suspension was heated at reflux for 20 minutes, then allowed to cool to room temperature. The mixture was taken into 250 ml of EtOAc and 200 ml of H2. The aqueous layer was extracted with 200 ml of EtOAc and the combined organics were washed twice with 250 ml of water and 100 ml of brine, dried over MgSO4, filtered and evaporated to obtain 15.7 g of the desired product as a solid.

Workup

  1. waitAfter a further 10 minutes
  2. temperaturethe suspension was heated
  3. temperatureat reflux for 20 minutes
  4. extractionThe aqueous layer was extracted with 200 ml of EtOAc
  5. washthe combined organics were washed twice with 250 ml of water and 100 ml of brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-cde7e681c41a47928ae7eb2e213796e5
Source dataset
uspto-grants-1995_05
Patent number
US05416112

Linked notes

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