Thionyl Chloride → 5-bromo-2-(chloromethyl)pyridine
反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8]O)=[N:6][CH:7]=1.S(Cl)([Cl:12])=O>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][Cl:12])=[N:6][CH:7]=1参加物
5
実験手順
To a stirred solution of (5-Bromo-pyridin-2-yl)-methanol (1 g, 5.319 mmol) in CH2Cl2 (20 mL) is added drop wise thionyl chloride (0.57 mL, 7.979 mmol) at 0° C. then stirred for another 4 hours. Reaction mixture is diluted with saturated sodium bicarbonate solution and extracted with CH2Cl2. Organic layer is dried over sodium sulphate, solvent is evaporated in vacuo and purified by column chromatography using 7% ethyl acetate in hexane as an eluent to afford the title compound (0.8 g). 1HNMR (400 MHz, DMSO-d6) δ: 4.7 (s, 2H), 7.53 (d, 8.36 Hz, 1H), 8.09-8.11 (dd, J1=2.44 Hz, J2=8.23 Hz, 1H), 8.69 (d, J=2.4 Hz, 1H), LC-MS (M/Z): [M+H]=206.0.
後処理
- customReaction mixture
- extractionextracted with CH2Cl2
- dry with materialOrganic layer is dried over sodium sulphate, solvent
- customis evaporated in vacuo
- custompurified by column chromatography
出典と根拠
- ORDレコード
- ord-60b1bca172bf41bb832e4b2326491fdb
- 出典データセット
- uspto-grants-2016_08
- 特許番号
- US09428528B2
反応ノート
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