Potassium Nitrate → 4-(Ethylsulfonyl)-1-fluoro-2-nitrobenzene

HRID 45407

反応式

HRID 45407 の反応式
[CH2:1]([S:3]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)(=[O:5])=[O:4])[CH3:2].[N+:13]([O-])([O-:15])=[O:14].[K+]>S(=O)(=O)(O)O>[CH2:1]([S:3]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]([N+:13]([O-:15])=[O:14])[CH:7]=1)(=[O:4])=[O:5])[CH3:2]

参加物

4

反応物 2

HCID 24434Potassium NitrateHCID 71814Fluoresone

生成物 1

HCID 673602634-(Ethylsulfonyl)-1-fluoro-2-nitrobenzene収率 66%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

反応条件

温度
90 °C

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.

後処理

  1. extractionthe mixture was extracted with ethyl acetate (25 ml)
  2. washwashed with water (20 ml) and brine (10 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (hexane/ethylacetate 1:3)
  6. customto give a light yellow solid which
  7. customwas crystallized from methanol

出典と根拠

ORDレコード
ord-f71feadad67f41ecaa39e431e9b6e979
出典データセット
uspto-grants-2013_09
特許番号
US08541476B2

関連ノート

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