Stannane, trimethyl(4-methylphenyl)- → 2-Cyano-4'-methyl-4-nitrobiphenyl

HRID 2255527Notes

Reaction equation

HRID 2255527 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([Sn](C)(C)C)=[CH:3][CH:2]=1.Br[C:13]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:14]=1[C:15]#[N:16]>C1(C)C=CC=CC=1.CCOC(C)=O.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:15]([C:14]1[CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=[CH:20][C:13]=1[C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)#[N:16]

Participants

6

Reactant 2

HCID 617834Stannane, trimethyl(4-methylphenyl)-HCID 70954232-Bromo-5-nitrobenzonitrile

Product 1

HCID 190122062-Cyano-4'-methyl-4-nitrobiphenylYield 74%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of p-tolyltrimethyltin (389 mg, 1.525 mmol) in dry toluene (5 mL) under N2 was added 2-bromo-5-nitro-benzonitrile (276 mg, 1.22 mmol) and Pd(PPh3)4 (176 mg; 10 mol %). The reaction was stirred at reflux under N2 for 24 hours and then cooled to room temperature. The mixture was diluted with EtOAc and the solid was removed by filtration through a pad of celite. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography on a silica column eluting with Hex/EtOAc (10:1) to afford 214 mg (74%) of the titled compound as a slightly yellow solid. 1H-NMR: (300 MHz, CDCl3) δ 2.42 (s, 3H), 7.32 (d, 2H), 7.48 (d, 2H), 7.69 (d, 1H), 8.45 (dd, 1H), 8.61 (s, 1H).

Workup

  1. temperatureat reflux under N2 for 24 hours
  2. customthe solid was removed by filtration through a pad of celite
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by flash chromatography on a silica column
  5. washeluting with Hex/EtOAc (10:1)

Sources & evidence

ORD record
ord-38ef312c1790459e846951e4ceeebe01
Source dataset
uspto-grants-1993_08
Patent number
US05240928

Reaction notes

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