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

HRID 1521943노트

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HRID 1521943 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-9c22a9f1bb3846c297b3deb79a3df96e
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073922B2

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