4-Fluorophenylacetyl chloride → HCID 68430510, compound

HRID 659957Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.C([Mg]Cl)(C)C.[F:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23](Cl)=[O:24])=[CH:18][CH:17]=1>O1CCCC1>[F:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=2)=[O:24])=[CH:18][CH:17]=1

Participants

Conditions

Temperature: -78 °C

Procedure

20 g (79 mmoles) of 4-iodo-2-methylthiopyrimidine in 165 mL of tetrahydrofuran under argon is cooled to −70° C. 45.5 mL of isopropylmagnesium chloride (2M in THF) is then slowly added to the reaction mixture, keeping the temperature at −70° C. After 30 min., a solution of 4-fluorophenyl acetyl chloride (13.7 g, 79 mmoles) in 65 mL tetrahydrofuran is added dropwise to the reaction mixture which is further stirred at −78° C. for 1 hour and allowed to reach 0° C. After 30 min. at 0° C., the reaction is poured into ice-water and extracted with ethyl acetate. The organic phase is washed with water and dried over magnesium sulfate. After concentration the oily purified by chromatography on silica gel (ethyl acetate/hexane 4/1) affording 9.5 g of 2-(4-Fluoro-phenyl)-1-(2-methylthio-pyrimidin-4-yl)-ethanone as yellow oil.

Workup

customat −70° C
customto reach 0° C
waitAfter 30 min. at 0° C.
extractionextracted with ethyl acetate
washThe organic phase is washed with water
dry with materialdried over magnesium sulfate
concentrationAfter concentration the
customoily purified by chromatography on silica gel (ethyl acetate/hexane 4/1)

Sources & evidence

ORD record: ord-b9ba12bb0c79476d9d6727c98de1d271
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084395B2

Reaction notes

Loading…