Potassium Carbonate → Biphenyl

HRID 514753Notes

Reaction equation

[N+]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1I)([O-])=O.C([O-])([O-])=O.[K+].[K+].[CH3:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].C(OCC)(=O)C>O1CCOCC1.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:4]1([C:19]2[CH:18]=[CH:17][CH:22]=[CH:21][CH:20]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 80 °C

Procedure

4,4,5,5-Tetramethyl-2-(4-indanone-1-yl)[1,3,2]-dioxoborolane (1.20 g, 4.6 mmol) and o-nitroiodobenzene (0.87 g, 4.6 mmol) were dissolved in a mixture of dioxane (10 mL) and water (2 mL). K2CO3 (1.28 g, 9.2 mmol) and Pd(PPh3)4 (0.27 g, 0.2 mmol) were added. The reaction mixture was heated in a flow of argon to 80° C., kept at this temperature over a period of 24 h (TLC monitoring: hexane/ethyl acetate, 4:1), cooled, and filtered through Celite. The filtrate was evaporated. The residue was dissolved in CH2Cl2. An undissolved precipitate was filtered off. The filtrate was partially evaporated, and the product was purified in a short silica gel column (hexane/ethyl acetate) to give 1.25 g of a product containing PPh3O. The product was cyclized without additional purification.

Workup

filtrationfiltered through Celite
customThe filtrate was evaporated
dissolutionThe residue was dissolved in CH2Cl2
filtrationAn undissolved precipitate was filtered off
customThe filtrate was partially evaporated
customthe product was purified in a short silica gel column (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-6779e7fffd814fa8b6d9810817e787f6
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108916B2

Reaction notes

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