反応 #73685

反応方程式

1-(ethylsulfonyl)-4-fluorobenzene

potassium nitrate

→

4-(Ethylsulfonyl)-1-fluoro-2-nitrobenzene

収率 66.0%

溶媒

sulfuric acid

反応条件

後処理

1. 1
   抽出the mixture was extracted with ethyl acetate (25 ml)
2. 2
   洗浄washed with water (20 ml) and brine (10 ml)
3. 3
   乾燥dried over sodium sulfate
4. 4
   濃縮concentrated
5. 5
   その他The residue was purified by column chromatography (hexane/ethylacetate 1:3)
6. 6
   その他to give a light yellow solid which
7. 7
   その他was crystallized from methanol

実験手順

To a solution of 1-(ethylsulfonyl)-4-fluorobenzene (1.36 mmol, 0.257 g) in sulfuric acid (1.32 ml) was added potassium nitrate (0.243 g) at 80° C. The mixture was stirred at 90° C. for 2 hours. Ice water (5 ml) was added and the mixture was extracted with ethyl acetate (25 ml) and washed with water (20 ml) and brine (10 ml). The organic extracts were combined and dried over sodium sulfate and concentrated. The residue was purified by column chromatography (hexane/ethylacetate 1:3) to give a light yellow solid which was crystallized from methanol. HPLC indicated 98% purity, mp 128-131° C., (0.21 g, 66% yield). 1H NMR (CDCl3): 1.35 (t, 3H, CH3), 3.21 (q, 2H, CH2), 7.55 (t, 1H, Ar—H), 8.21 (m, 1H, Ar—H), 8.64 (d, 1H, Ar—H); MS: 229 M−. Elemental Analysis (C, H, N, F, S) for C8H8FNO4S; calculated C, 41.20; H, 3.46; N, 6.01; F, 8.15; S, 13.75. found C, 41.31; H, 3.35; N, 5.85; F, 8.17; S, 13.53.

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