Ethanol → 4-Cyclohexen-1-yl-3-fluorobenzonitrile

HRID 1485111Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1I)[C:5]#[N:6].[C:11]1(B(O)O)[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=1.C(O)C.[O-]CC.[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(Cl)(Cl)Cl.O>[C:11]1([C:9]2[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=2[F:1])[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a mixture of 3-fluoro-4-iodobenzonitrile (1.53 g), 1-cyclohexen-1-yl-boronic acid (938 mg), bis(triphenylphosphine)palladium(II) dichloride (435 mg) and ethanol (9.75 mL), sodium ethoxide (about 20%, solution in ethanol, 5.75 mL) was added and the mixture was stirred at 90° C. for 15 minutes under irradiation with microwaves. After being cooled to room temperature, the reaction mixture was poured into water and three extractions were conducted with chloroform. The combined organic layers were washed with saturated brine and passed through a phase separator to be concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=100:0-75:25) to give the titled compound as a pale yellow oil (980 mg).

Workup

additionwas added
temperatureAfter being cooled to room temperature
washThe combined organic layers were washed with saturated brine
concentrationto be concentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=100:0-75:25)

Sources & evidence

ORD record: ord-276de4b7010c42ada4c1c5af8540d4ef
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422240B2

Reaction notes

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