Tetrahydrofuran → 1-(5-Bromopyrimidin-2-yl)ethan-1-one
反応式
[Br:1][C:2]1[CH:3]=[N:4][C:5](C#N)=[N:6][CH:7]=1.C[Mg]Br.[CH2:13]1[CH2:17][O:16]CC1>>[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:17](=[O:16])[CH3:13])=[N:6][CH:7]=1参加物
4
反応条件
- 温度
- -78 °C
実験手順
To a solution of 5-bromopyrimidine-2-carbonitrile (221 mg, 1.2 mmol) in THF (10 ml) was added methylmagnesium bromide (3.0 ml, 4.20 mmol, 1.4 molar, THF) at −78° C. under nitrogen. The solution was stirred at −78° C. for 3.5 hours, and then quenched with satd aq NH4Cl, and extracted with EtOAc. The combined organic layer was dried over anhydrous Na2SO4 and concentrated. The reaction was purified by column chromatography on silica gel (petroleum ether: EtOAc=1:0 to 0:1) to afford 1-(5-bromopyrimidin-2-yl)ethanone (1.55 mg, 61% yield). 1H NMR (CDCl3 500 MHz): δ 9.00 (s, 2H), 2.80 (s, 3H).
後処理
- customquenched with satd aq NH4Cl
- extractionextracted with EtOAc
- dry with materialThe combined organic layer was dried over anhydrous Na2SO4
- concentrationconcentrated
- customThe reaction was purified by column chromatography on silica gel (petroleum ether: EtOAc=1:0 to 0:1)
出典と根拠
- ORDレコード
- ord-71a37e665ded4f3a9f8e1cbfe2daea43
- 出典データセット
- uspto-grants-2015_08
- 特許番号
- US09108938B2
反応ノート
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