Hexane → HCID 66846862, compound

HRID 1466623Notes

Reaction equation

C([Li])CCC.CCCCCC.Cl[CH2:13][CH2:14][I:15].[CH3:16][O:17][C:18]1C=C[C:21]([C:24]([F:27])([F:26])[F:25])=[N:22][CH:23]=1>C1COCC1>[I:15][C:14]1[C:18]([O:17][CH3:16])=[CH:23][N:22]=[C:21]([C:24]([F:27])([F:26])[F:25])[CH:13]=1

Participants

Conditions

Temperature: -78 °C

Procedure

In an oven-dried flask, 5-methoxy-2-(trifluoromethyl)pyridine was dissolved in THF (20 mL). This mixture was cooled at −78° C., and then 2.5 M n-butyllithium in hexane (2.60 mL, 6.5 mmol) was added. After stirring at this same temperature for 40 minutes, 1-chloro-2-iodoethane (0.60 mL, 6.6 mmol) was added. The reaction was kept at −78° C. for an additional 30 minutes, and then quenched with saturated aqueous ammonium chloride. The mixture was warmed to room temperature, partitioned between ethyl acetate and water, and the organic layer dried with magnesium sulfate and evaporated in vacuo. The crude product was purified via flash chromatography on silica gel (0 to 40% ethyl acetate in heptanes) to yield 0.3128 g (16%) of 4-iodo-5-methoxy-2-(trifluoromethyl)pyridine. 1H NMR (400 MHz, DMSO-d6) δ: 8.38 (s, 1H), 8.29 (s, 1H), 4.05 (s, 3H).

Workup

waitThe reaction was kept at −78° C. for an additional 30 minutes
customquenched with saturated aqueous ammonium chloride
temperatureThe mixture was warmed to room temperature
custompartitioned between ethyl acetate and water
dry with materialthe organic layer dried with magnesium sulfate
customevaporated in vacuo
customThe crude product was purified via flash chromatography on silica gel (0 to 40% ethyl acetate in heptanes)

Sources & evidence

ORD record: ord-0b9882be54734537bb5968223dd041db
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999998B2

Reaction notes

Loading…