ChemicalBook CAS DataBase List 2-chloro-1-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)ethanone

2-chloro-1-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)ethanone synthesis

9synthesis methods

Product Name:2-chloro-1-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)ethanone
CAS Number:943126-72-5
Molecular formula:C11H10ClFO2
Molecular Weight:228.65

Sulfur, [2-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)-2-oxoethylidene]dimethyloxo-

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2-chloro-1-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)ethanone

943126-72-5
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Yield: 78%

Reaction Conditions:

Stage #1:dimethylsulfoxonium-2-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)-2-oxoethylide with methanesulfonic acid;lithium chloride in tetrahydrofuran at 0 - 70; for 18.8333 h;
Stage #2: with water;sodium hydrogencarbonate in tetrahydrofuran

Steps:

6
Example 6 Synthesis of2-chloro-l-(6-fluoro-3,4-dihvdro-2H-chromen-2-yl) ethanone A solution of dimethylsulfoxonium-2-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)-2- oxoethylide (0.90 g, 3.26 mmol, 97.9 A%) in THF (12 ml) under mechanical stirring and under nitrogen was cooled to 0°C and to this was added lithium chloride (0.179 g, 4.22 mmol). The methanesulfonic acid (0.267 ml, 4.03 mmol) was loaded dropwise at 0°C in a 10 min. interval. The reaction mixture was heated to 20⁰C in 10 min and then to 70⁰C in a 30 min. interval. The reaction was kept under stirring for 2 hours at 7O⁰C and then cooled to 20⁰C. After 16 hours, a saturated aqueous solution of NaHCO₃ (10 ml) was added and strata were then separated. The organic phase was diluted with toluene (20 ml) and concentrated by reduced pressure to obtain a dry residue (0.78 g). This residue was dissolved again in toluene and washed with a saturated solution of NaHCO₃ (20 ml). The organic phase was further washed with demi water (20 ml) and brine (20 ml) and then dried under vacuum to give raw 2- chloro-l-(6-fluoro-3,4-dihydro-2H-chromen-2-yl) ethanone as a brown oil (0.66 g, 78% yield, 88.4 A%). δ_H(400 MHz; CDCl₃) 6.86-6.83 (2H, m, Ar), 6.80-6.75 (IH, m, Ar), 4.69-4.65 (IH, m), 4.63 (IH, d, J 16.8), 4.47 (IH, d, J 16.8), 2.91-2.72 (2H, m), 2.34-2.26 (IH, m), 2.13-2.03 (IH, m); m/z (EI) 228.035339 (M⁺. C_{1 1}H_I0CIFO₂ requires 228.03551).