Potassium Carbonate → HCID 22057729, compound

HRID 1828710Notes

Reaction equation

Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH2:10][CH3:11].[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+].[NH4+].[Cl-]>CN(C=O)C.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>[CH2:10]([C:3]1[CH:4]=[C:5]([C:6]#[N:7])[CH:8]=[CH:9][C:2]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:11]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 4-bromo-3-ethyl benzonitrile (1 g, 4.76 mmol), phenylboronic acid (1.16 g, 9.5 mmol), K2CO3 (1.97 g, 14.3 mmol), and Pd(PPh3)4 (543 mg, 0.48 mmol) in DMF (anhydrous, 15 mL) is heated in a sealed tube at 120° C. for 12 h. After cooling to room temperature, the reaction mixture is poured into a mixture of ice and saturated aqueous NH4Cl. The mixture is extracted with EtOAc (3×30 mL). The combined organic layers are washed with saturated aqueous NaCl, dried over Na2SO4, and concentrated. The crude product obtained is purified by silica gel chromatography (5% EtOAc in hexanes) to give 2-ethyl-biphenyl-4-carbonitrile as a colorless oil.

Workup

temperatureAfter cooling to room temperature
extractionThe mixture is extracted with EtOAc (3×30 mL)
washThe combined organic layers are washed with saturated aqueous NaCl
dry with materialdried over Na2SO4
concentrationconcentrated
customThe crude product obtained
customis purified by silica gel chromatography (5% EtOAc in hexanes)

Sources & evidence

ORD record: ord-ffd18a6920074f0c918ea703a843d42d
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07060697B2

Reaction notes

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