Water → 4-(Pentafluoro-lambda6-sulfanyl)benzaldehyde

HRID 1672571Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][C:5]([S:8]([F:13])([F:12])([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[CH3:14]N(C)P(N(C)C)(N(C)C)=O.[C]=O.[OH2:27]>C(#N)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>[CH:7]1[C:2]([CH:14]=[O:27])=[CH:3][CH:4]=[C:5]([S:8]([F:13])([F:12])([F:11])([F:10])[F:9])[CH:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 4-iodophenylsulfur pentafluoride (250 mg, 0.757 mmol) in acetonitrile (10 mL) was added to a 100 mL pressure bottle containing tetrakis(triphenylphosphine)palladium(0) (43.8 mg, 0.038 mmol), hexamethylphosphoramide (1.25 mL, 7.18 mmol), and poly(methylhydrosiloxane) (1.0 mL, 0.76 mmol). The reaction was pressurized with carbon monoxide (50 psi), and stirred for 20 hr at 80° C. The mixture was cooled to ambient temperature, water (100 mL) was added, and the product was extracted with Et2O (2×100 mL). The organic layer was washed with brine and dried over Na2SO4, filtered, and concentrated in vacuo to a yellow oil. The crude product was chromatographed on silica gel (Analogix® SF10-8G column, 0%-25% EtOAc/hexanes, 10 mL/min) to give 151 mg (86%) of the title compound as a colorless liquid. 1H NMR (300 MHz, DMSO-d6) δ 10.12 (s, 1H), 8.21-8.08 (m, 4H).

Workup

temperatureThe mixture was cooled to ambient temperature
extractionthe product was extracted with Et2O (2×100 mL)
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo to a yellow oil
customThe crude product was chromatographed on silica gel (Analogix® SF10-8G column, 0%-25% EtOAc/hexanes, 10 mL/min)

Sources & evidence

ORD record: ord-d078c473650c43609bc53e5aa2d48076
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998993B2

Reaction notes

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