반응 #10325

반응 방정식

3-methylbenzothiophene

SELECTFLUOR

→

2-fluoro-3-methyl-1-benzothiophene

수율 72.0%

용매

acetonitrile

반응 조건

후처리

1. 1
   기타The solvent was removed in vacuo
2. 2
   세척washed with sodium hydrogen carbonate solution, water and brine
3. 3
   건조dried over MgSO4
4. 4
   기타evaporated in vacuo
5. 5
   기타Purification by flash column chromatography on silica
6. 6
   세척eluting with isohexane

실험 절차

A stirred solution of 3-methylbenzothiophene (0.51 g, 3.37 mmol) in acetonitrile (5 μL) under nitrogen was treated with SELECTFLUOR™ (1.25 g, 3.35 mmol) and heated to 70° C. overnight. The solvent was removed in vacuo. The residue was taken up in ethyl acetate and washed with sodium hydrogen carbonate solution, water and brine, dried over MgSO4 and evaporated in vacuo. Purification by flash column chromatography on silica, eluting with isohexane, gave 2-fluoro-3-methyl-1-benzothiophene (72% pure, 190 mg, 0.82 mmol) which was treated according to the method of Example 29 Step 2 to give 3-(bromomethyl)-2-fluoro-1-benzothiophene (95 mg, 12%). 1H NMR (500 MHz, CDCl3) δ 7.75 (1H, d, J=8.0 Hz), 7.68 (1H, d, J=8.0 Hz), 7.46 (1H, t, J=7.6 Hz), 7.39–7.35 (1H, m), 4.65 (2H, s).

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