1-Bromo-4-nitrobenzene → 2-Methoxy-4'-nitro-1,1'-biphenyl

HRID 25746

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1B(O)O>COCCOC.C(=O)([O-])[O-].[Na+].[Na+]>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 20.8 g of 4-bromonitrobenzene and 17.2 g of 2-methoxyphenyl boronic acid in 340 mL of ethylene glycol dimethyl ether and 170 mL of 2 M sodium carbonate solution was purged with argon gas and then 3.6 g of Pd(PPh3)2Cl2 was added under argon atmosphere. The reaction mixture was heated in a sealed flask at 120° C. overnight. The reaction mixture was cooled down to room temperature. The mixture was filtered through diatomaceous earth and the filtrate was diluted with water and the product was extracted three times with EtOAc. The organic layers were combined, dried over magnesium sulfate (MgSO4), and the solvent was evaporated in vacuo. The residue was purified by flash chromatography to yield 17.1 g of 2-methoxy-4′-nitrobiphenyl as a solid.

Workup

customwas purged with argon gas
addition3.6 g of Pd(PPh3)2Cl2 was added under argon atmosphere
temperatureThe reaction mixture was cooled down to room temperature
filtrationThe mixture was filtered through diatomaceous earth
additionthe filtrate was diluted with water
extractionthe product was extracted three times with EtOAc
dry with materialdried over magnesium sulfate (MgSO4)
customthe solvent was evaporated in vacuo
customThe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-6e5a00daa6644cc593f8f07d843498b7
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06858627B2

Linked notes

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