Toluene → 1-Cyclobutyl-4-nitro-2-(trifluoromethyl)benzene

HRID 1485078Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[CH:15]1(B(O)O)[CH2:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(C)C=CC=CC=1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[CH:15]1([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=2[C:11]([F:14])([F:13])[F:12])[CH2:18][CH2:17][CH2:16]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-iodo-5-nitrobenzotrifluoride (4.62 g), cyclobutylboronic acid (4.15 g), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (4.15 g), cesium carbonate (22.6 g), toluene (67.0 mL) and water (33.0 mL) was stirred in a sealed tube at 80° C. for 6 hours. After cooling the reaction mixture to room temperature, extraction was conducted with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate and after removing the desiccant by filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=100:0-94:6) to give 1-cyclobutyl-4-nitro-2-(trifluoromethyl)benzene as a pale yellow oil (1.69 g).

Workup

temperatureAfter cooling the reaction mixture to room temperature
extractionextraction
dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
customafter removing the
filtrationdesiccant by filtration
concentrationthe filtrate was concentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=100:0-94:6)

Sources & evidence

ORD record: ord-a54d827d309a45b0b43407b8db30ef0c
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422240B2

Reaction notes

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