1-Chloro-2-nitrobenzene → 2-Nitrobiphenyl

HRID 1014778Notes

Reaction equation

HRID 1014778 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[F-].[Cs+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2C=CC=CC=2)C2[C-](N(C)C)C=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2]>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O-:10])=[O:9]

Participants

7

Reactant 3

HCID 69451-Chloro-2-nitrobenzeneHCID 25953Cesium fluorideHCID 66827Phenylboronic Acid

Product 1

HCID 68292-NitrobiphenylYield 73.3%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1317290462-Diphenylphosphino-dimethylaminoferroceneCatalystHCID 312751,4-DioxaneSolvent

Procedure

According to General Procedure A, a mixture of o-chloronitrobenzene (79 mg, 0.50 mmol), phenylboronic acid (91 mg, 0.75 mmol), CsF (228 mg, 1.50 mmol), Pd(OAc)2 (2 mg, 0.01 mmol) and 12f (8 mg, 0.02 mmol) in 1,4-dioxane (2.5 mL) has heated to reflux, cooled and filtered. Evaporation of the solvent under reduced pressure and column chromatography of the pre-adsorbed crude material (1% Et2O in hexane, silica gel) gave 51d (73 mg, 73%) as a bright yellow oil. 1H NMR (300 MHz, CDCl3) δ 7.86 (d, 1H, J=8.0 Hz), 7.62 (t, 1H, J=7.5 Hz), 7.51-7.40 (m, 5H), 7.34-7.31 (m, 2H); 13C NMR (75.5 MHz, CDCl3) δ 149.3, 137.4, 136.3, 132.2, 131.9, 128.7, 128.2, 128.1, 127.9, 124.0.

Workup

  1. temperaturehas heated
  2. temperatureto reflux
  3. temperaturecooled
  4. filtrationfiltered
  5. customEvaporation of the solvent under reduced pressure and column chromatography of the pre-adsorbed crude material (1% Et2O in hexane, silica gel)

Sources & evidence

ORD record
ord-a47bdbb7185948bcb8a8e03e58ab89c8
Source dataset
uspto-grants-2011_07
Patent number
US07982064B2

Reaction notes

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