Hydrochloric Acid → 2-Methyl-5-nitrobiphenyl

HRID 383067Notes

Reaction equation

HRID 383067 reaction equation
Br[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH3:11].[C:12]1(OB(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>CN(C=O)C.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>[N+:8]([C:6]1[CH:5]=[CH:4][C:3]([CH3:11])=[C:2]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=1)([O-:10])=[O:9]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 78412Phenyl dihydrogen orthoborateHCID 821892-Bromo-4-nitrotoluene

Product 1

HCID 107510832-Methyl-5-nitrobiphenylYield 57.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2-Bromo-4-nitrotoluene (2.16 g, 10.00 mmol) and phenylboric acid (1.46 g, 12.00 mmol) were dissolved in anhydrous DMF (25 mL) under nitrogen. To this mixture was added Pd(Ph3P)4 (0.58 g, 5%). The mixture was heated at 100° C. overnight. The solution was poured onto 1N HCl and extracted with Et2O. The crude product was chromatographed on silica gel using hexanes as eluent. After recrystallization from ethanol, the desired product (1.23 g) was obtained as pale orange needles: m.p. 69-71° C.;

Workup

  1. extractionextracted with Et2O
  2. customThe crude product was chromatographed on silica gel
  3. customAfter recrystallization from ethanol

Sources & evidence

ORD record
ord-8834ba2c76b04810a36f2e1faf3a799e
Source dataset
uspto-grants-2001_10
Patent number
US06310095B1

Reaction notes

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