Water → 4'-Methyl-2-nitro-1,1'-biphenyl

HRID 1909

Reaction equation

HRID 1909 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4](B(O)O)=[CH:3][CH:2]=1.Br[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19].O.CC(O)C>[OH-].[Na+].C1C=CC=CC=1>[CH3:10][C:1]1[CH:6]=[CH:5][C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N+:18]([O-:20])=[O:19])=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 113411-Bromo-2-nitrobenzeneHCID 79799Tolylboronic acid

Product 1

HCID 104431944'-Methyl-2-nitro-1,1'-biphenylYield 77.4%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A vigorously stirred mixture of 34 g (0.25 mol) of 4-tolylboronic acid and 34 g (0.17 mol) of 2-bromo-1-nitrobenzene in a mixture of 170 mL of 5N sodium hydroxide, 57 mL of water, 215 mL of 2-propanol and 1080 mL of benzene was treated with 11.9 g of (tetrakis)triphenylphosphine palladium(0). The two-phase mixture was heated at reflux for three hours. The cooled reaction mixture was filtered through Celite and the filter cake washed with fresh benzene. The organic layer was separated and washed with water (3×), dried over magnesium sulfate and filtered. The filtrate was evaporated under vacuum and the residue (46.1 g) purified by preparative high pressure liquid chromatography on silica gel, eluting with hexane/ethyl acetate (20:1), to give 28.05 g of the product.

Workup

  1. temperatureThe two-phase mixture was heated
  2. temperatureat reflux for three hours
  3. customThe cooled reaction mixture
  4. filtrationwas filtered through Celite
  5. washthe filter cake washed with fresh benzene
  6. customThe organic layer was separated
  7. washwashed with water (3×)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customThe filtrate was evaporated under vacuum
  11. customthe residue (46.1 g) purified by preparative high pressure liquid chromatography on silica gel
  12. washeluting with hexane/ethyl acetate (20:1)

Sources & evidence

ORD record
ord-eb2559d3fc404f17a5ecee988d37d685
Source dataset
uspto-grants-1998_03
Patent number
US05726319

Linked notes

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