反応 #10325

反応方程式

3-methylbenzothiophene

SELECTFLUOR

→

2-fluoro-3-methyl-1-benzothiophene

収率 72.0%

溶媒

acetonitrile

反応条件

後処理

1. 1
   その他The solvent was removed in vacuo
2. 2
   洗浄washed with sodium hydrogen carbonate solution, water and brine
3. 3
   乾燥dried over MgSO4
4. 4
   その他evaporated in vacuo
5. 5
   その他Purification by flash column chromatography on silica
6. 6
   洗浄eluting with isohexane

実験手順

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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