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

HRID 45407

반응식

HRID 45407 반응식
[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]

참가 물질

4

반응물 2

HCID 24434Potassium NitrateHCID 71814Fluoresone

생성물 1

HCID 673602634-(Ethylsulfonyl)-1-fluoro-2-nitrobenzene수율 66%

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

반응 조건

온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f71feadad67f41ecaa39e431e9b6e979
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541476B2

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