Water → 4'-Methyl-3-nitro-1,1'-biphenyl
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6](B(O)O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[Na+].[Na+].O.Br[C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=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.C(O)C.C1(C)C=CC=CC=1>[CH3:27][C:24]1[CH:25]=[CH:26][C:21]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[CH:22][CH:23]=1Participants
8
Conditions
- Temperature
- 70 °C
Procedure
Under an inert atmosphere was added 3-nitrobenzene boronic acid (6.3 mmol) and sodium carbonate (11.6 mmol) to water (8 mL), toluene (8 mL) and ethanol (8 mL) and stirred for 5 minutes. p-Bromotoluene (5.8 mmol) and tetrakis(triphenylphosphine)palladium (0.3 mmol) added and heated to 70° C. for 7 hours. Concentrated under reduced pressure and extracted into chloroform (3×20 mL). The organics were then washed with 10% sodium bicarbonate (10 mL), water (10 mL) and brine (10 mL) before drying over sodium sulfate, filtering and evaporating to dryness. The residue was then purified by column chromatography and taken onto the next stage.
Workup
- concentrationConcentrated under reduced pressure
- extractionextracted into chloroform (3×20 mL)
- washThe organics were then washed with 10% sodium bicarbonate (10 mL), water (10 mL) and brine (10 mL)
- dry with materialbefore drying over sodium sulfate
- filtrationfiltering
- customevaporating to dryness
- customThe residue was then purified by column chromatography
Sources & evidence
- ORD record
- ord-dc9b3b22ce6c451fa0ea7edc00434982
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07482469B2
Reaction notes
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