Potassium Carbonate → 1,1'-(2-Nitro-[1,1'-biphenyl]-4,4'-diyl)diethanone

HRID 337391Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[C:14]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)(=[O:16])[CH3:15].C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.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>[N+:11]([C:3]1[CH:4]=[C:5]([C:8](=[O:10])[CH3:9])[CH:6]=[CH:7][C:2]=1[C:20]1[CH:21]=[CH:22][C:17]([C:14](=[O:16])[CH3:15])=[CH:18][CH:19]=1)([O-:13])=[O:12]

Participants

Conditions

Temperature: 110 °C

Procedure

1-(4-bromo-3-nitrophenyl)ethanone (2 g, 8.20 mmol) and (4-acetylphenyl)boronic acid (2.016 g, 12.29 mmol), aq.K2CO3 (2M, 12.08 mL, 24.17 mmol) and Pd(PPh3)4 (0.33 g, 0.286 mmol) were dissolved in toluene (40 mL) and heated at 110° C. for 2 days. The crude product was extracted with DCM and purified on silica gel (0-100% EtOAc/Hexane). Fractions were concentrated to give the title compound as a white solid.

Workup

extractionThe crude product was extracted with DCM
custompurified on silica gel (0-100% EtOAc/Hexane)
concentrationFractions were concentrated

Sources & evidence

ORD record: ord-5888ef84265e42a29b1c8e06e2dd6979
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889726B2

Reaction notes

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