Hydrochloric Acid → 2-Methyl-5-nitrobiphenyl

HRID 1739136Notes

Reaction equation

HRID 1739136 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>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.CN(C=O)C>[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 phenyl boric acid (1.46 g, 12.00 mmol) were dissolved into 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 material was chromatographed on silica gel using hexanes as an eluent. After recrystallization from ethanol, 1.23 g (57.6%) of pale orange needles were obtained. mp 69-71° C.; 1H NMR (CDCl3) 2.36 (3H, s), 7.29-7.40 (2H, m), 7.41-7.49 (5H,m), 8.07-8.10 (2H, m); 13C NMR (CDCl3) 20.68, 121.96, 124.51, 127.78, 128.41, 128.83, 131.06, 139.44, 142.97, 143.48, 146.05; anal calc. for C13H11NO21, C:73.26, H:5.20, N:6.57; found, C:73.10, H:5.12, N:6.50; m/z (EI) 213; HRMS calc. for C13H11NO2, 213.0790; found, 213.0793.

Workup

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

Sources & evidence

ORD record
ord-6099a8a7868f4e639cea49b0eb0986b1
Source dataset
uspto-grants-1999_10
Patent number
US05965539

Reaction notes

Loading…