Cyclohexane → 4-Methyl-3-nitro-1,1'-biphenyl

HRID 1193867Notes

Reaction equation

HRID 1193867 reaction equation
[C:1]1([Li])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1CCCCC1.I[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([N+:22]([O-:24])=[O:23])[CH:16]=1>CCOCC.C1COCC1.Cl.[Cl-].[Zn+2].[Cl-].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:1]1([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([N+:22]([O-:24])=[O:23])[CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

9

Reactant 3

HCID 8078CyclohexaneHCID 1704814-Iodo-2-nitrotolueneHCID 178506676HCID 178506676, compound

Product 1

HCID 129098264-Methyl-3-nitro-1,1'-biphenylYield 85%

Reagents, catalysts & solvents 5

HCID 3007855ZincchlorideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Phenyllithium (10 ml of a 2.0M solution in a 7:3 mixture of cyclohexane and ether, 20 mmol) was added dropwise to zinc chloride (20 ml of a 1.0M solution in ether, 20 mmol) at room temperature. The resulting mixture was stirred for 2 hours, then a solution of 4-iodo-2-nitrotoluene (2.63 g, 10 mmol) in THF (20 ml) and tetrakis(triphenylphosphine)palladium (0.3 g, 0.26 mmol) were added successively. The reaction mixture was stirred for 3 hours then diluted with 0.5M hydrochloric acid (40 ml) and extracted with ether (3×70 ml). The ether extracts were washed with brine, dried, concentrated then purified by column chromatography using petrol (60°-80° C.)-ethyl acetate (9:1) on silica gel to give 4-phenyl-2-nitrotoluene (1.8 g, 85% yield) as a yellow oil.

Workup

  1. stirringThe reaction mixture was stirred for 3 hours
  2. extractionextracted with ether (3×70 ml)
  3. washThe ether extracts were washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customthen purified by column chromatography
  7. custompetrol (60°-80° C.)-ethyl acetate (9:1)

Sources & evidence

ORD record
ord-4776b8af320a493f9e61978559b649b3
Source dataset
uspto-grants-1989_03
Patent number
US04812162

Reaction notes

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