Benzyl Alcohol → 6-(Benzyloxy)-2-bromo-3-chloropyridine

HRID 1521943ノート

反応式

HRID 1521943 の反応式
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[Br:15][C:16]1[C:21]([Cl:22])=[CH:20][CH:19]=[C:18](F)[N:17]=1>O1CCCC1.C(OCC)(=O)C.O>[CH2:1]([O:8][C:18]1[N:17]=[C:16]([Br:15])[C:21]([Cl:22])=[CH:20][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 3

HCID 244Benzyl AlcoholHCID 23665647Potassium tert-butoxideHCID 754123402-Bromo-3-chloro-6-fluoropyridine

生成物 1

HCID 904122516-(Benzyloxy)-2-bromo-3-chloropyridine

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To a solution of benzyl alcohol (55.5 mg, 0.513 mmol) in tetrahydrofuran (5 mL) at 0° C. was added potassium tert-butoxide (57.6 mg, 0.513 mmol) and the mixture was stirred at 0° C. for 2 hours. The mixture was cooled to −78° C. and a solution of 2-bromo-3-chloro-6-fluoropyridine (120 mg, 0.570 mmol) in 2 mL tetrahydrofuran was added. After stirring at −78° C. for 1 hour the mixture was diluted with ethyl acetate and water. The organic layer was separated, washed with water and brine, dried over sodium sulfate and concentrated. Purification by column chromatography (silica gel, 20% ethyl acetate in hexane) afforded the title compound. LCMS: 299.9 (M+3)+.

後処理

  1. temperatureThe mixture was cooled to −78° C.
  2. stirringAfter stirring at −78° C. for 1 hour the mixture
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customPurification by column chromatography (silica gel, 20% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-9c22a9f1bb3846c297b3deb79a3df96e
出典データセット
uspto-grants-2015_07
特許番号
US09073922B2

反応ノート

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