反応式
F[C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[OH:12][CH2:13][C:14]1([CH2:17][OH:18])[CH2:16][CH2:15]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[I:8][C:5]1[CH:6]=[CH:7][C:2]([O:12][CH2:13][C:14]2([CH2:17][OH:18])[CH2:16][CH2:15]2)=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1参加物
反応条件
- 温度
- 50 °C
実験手順
A solution of 1-fluoro-4-iodo-2-nitrobenzene (2.50 g, 9.4 mmol) in DMF (30 mL) was treated with 1-(hydroxymethyl)cyclopropylmethanol (1.91 g, 19 mmol) and K2CO3 (2.6 g, 19 mmol) and the mixture was heated at 50° C. for 8 hours. TLC indicated complete consumption of the arylfluoride. The mixture was diluted with water and extracted with ethyl acetate. The combined organics were washed with brine, dried over sodium sulfate and concentrated by rotoevaporation. Purification by flash column chromatography (EtOAc in heptanes) gave the titled compound as a light yellow solid (2.31 g, 71% yield). 1H NMR (400 MHz, DMSO) δ 8.15 (d, J=2.2 Hz, 1H), 7.92 (dd, J=8.8, 2.2 Hz, 1H), 7.17 (d, J=8.9 Hz, 1H), 4.60 (t, J=5.6 Hz, 1H), 4.05 (s, 2H), 3.36 (d, J=5.6 Hz, 2H), 0.50 (s, 4H).
後処理
- customconsumption of the arylfluoride
- additionThe mixture was diluted with water
- extractionextracted with ethyl acetate
- washThe combined organics were washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated by rotoevaporation
- customPurification by flash column chromatography (EtOAc in heptanes)
出典と根拠
- ORDレコード
- ord-af1aafb3e9064f4bac3bdba56441a578
- 出典データセット
- uspto-grants-2015_05
- 特許番号
- US09034866B2
関連ノート
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