Cesium fluoride → 7,8-Dichloro-1-(trifluoromethyl)-2,3,4,9-tetrahydro-1H-carbazol-1-ol

HRID 877495Notes

Reaction equation

[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]2[C:5]([C:6]3[CH2:7][CH2:8][CH2:9][C:10](=[O:16])[C:11]=3[NH:12]2)=[CH:4][CH:3]=1.[C:17]([Si](C)(C)C)([F:20])([F:19])[F:18].[F-].[Cs+]>C1COCC1>[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]2[C:5]([C:6]3[CH2:7][CH2:8][CH2:9][C:10]([C:17]([F:20])([F:19])[F:18])([OH:16])[C:11]=3[NH:12]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

7,8-Dichloro-2,3,4,9-tetrahydro-1H-carbazol-1-one (0.2 g, 0.78 mmol) was dissolved in anhydrous THF (5 mL), cooled to 0° C., and CF3TMS (1.2 mL, 8.7 mmol) followed by CsF (0.36 mg, 2.3 mmol) were added and stirred for 30 min. at 0° C. The reaction mixture was slowly warmed to room temperature and stirred for an additional 2 h, quenched with saturated NH4Cl and extracted with EtOAc (3×20 mL). The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to give the crude compound which was purified by column chromatography [EtOAc-hexane (1:4) as eluant] to provide the title compound as a yellow syrup (0.05 g, 19%). 1H NMR (500 MHz, CDCl3, δ in ppm) 8.32 (bs, 1H), 7.38 (d, J=8.5 Hz, 1H), 7.21 (d, J=8.5 Hz, 1H), 2.85-2.81 (m, 1H), 2.73-2.70 (m, 1H), 2.68 (s, 1H), 2.29-2.24 (m, 1H), 2.13-2.11 (m, 2H), 2.03-2.01 (m, 1H).

Workup

additionwere added
temperatureThe reaction mixture was slowly warmed to room temperature
stirringstirred for an additional 2 h
customquenched with saturated NH4Cl
extractionextracted with EtOAc (3×20 mL)
dry with materialThe combined organic extracts were dried over Na2SO4
concentrationconcentrated in vacuo
customto give the crude compound which
customwas purified by column chromatography [EtOAc-hexane (1:4) as eluant]

Sources & evidence

ORD record: ord-0fb6a9c1c3bd408eb24e69caab2be3f8
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987319B2

Reaction notes

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