3-Fluoroisonicotinaldehyde → 3-(4-Fluorobenzenesulfonyl)pyridine-4-carbaldehyde

HRID 1944388Notes

Reaction equation

F[C:2]1[CH:9]=[N:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[Na+].[F:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([O-:20])=[O:19])=[CH:14][CH:13]=1>CS(C)=O>[F:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([C:2]2[CH:9]=[N:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 3-fluoroisonicotinaldehyde (0.25 mL) in dimethyl sulfoxide (2.0 mL) was treated with a solution of 4-fluorobenzene sulfinic acid sodium salt (0.5 g) in dimethyl sulfoxide (3.0 mL), and the resulting mixture was stirred at 100° C. for 3 days. The mixture was cooled to room temperature, partitioned between water and ethyl acetate (20 mL), and the aqueous phase extracted with ethyl acetate. The combined organic solution was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with a mixture of dichloromethane and ethyl acetate (1:0 to 4:1 by volume) to afford the title compound as a white solid (0.38 g).

Workup

temperatureThe mixture was cooled to room temperature
custompartitioned between water and ethyl acetate (20 mL)
extractionthe aqueous phase extracted with ethyl acetate
dry with materialThe combined organic solution was dried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography on silica gel
washeluting with a mixture of dichloromethane and ethyl acetate (1:0 to 4:1 by volume)

Sources & evidence

ORD record: ord-6c0595f1422d4a3ea9db7f857c8ab656
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394836B2

Reaction notes

Loading…