1-Chloro-4-nitrobenzene → Biphenyl, 2-methyl-4'-nitro-

HRID 412802Notes

Reaction equation

HRID 412802 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B(O)O.[F-].[K+]>C1COCC1>[CH3:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 74741-Chloro-4-nitrobenzeneHCID 522689Potassium FluorideHCID 27332672-Methylphenyl boronic acid

Product 1

HCID 36415Biphenyl, 2-methyl-4'-nitro-Yield 98.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Chloronitrobenzene (80 mg, 0.51 mmol) reacted with o-methylphenylboronic acid (85 mg, 0.63 mmol) using 0.5/1.0 mol % of Pd(OAc)2/Ph5FcP(t-Bu)2 and KF (87 mg, 1.55 mmol) in THF solvent at 50° C. for 22 h to give the title compound (107 mg, 98%): 1H-NMR (500 MHz, CDCl3): δ 8.30 (d, 2H, J=6.90 Hz, aryl coupling 1.8 Hz), 7.51 (d, 2H, J=6.92 Hz, aryl coupling 1.8 Hz), 7.35-7.23 (m, 4H), 2.29 (s, 3H, Ar—CH3). 13C{1H}-NMR (125 MHz, CDCl3): δ 148.80, 146.86, 139.60, 135.04, 130.70, 130.09, 129.39, 128.45, 126.11, 123.40, 20.31. GC/MS(EI): m/z 213 (M+), 165, 152.

Workup

  1. customat 50° C.
  2. customfor 22 h

Sources & evidence

ORD record
ord-dd53b2398a2340fdb87d72801d6573f1
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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