Phosphorus tribromide → 3-Bromo-5-(bromomethyl)-2-(2,4-difluorophenoxy)pyridine

HRID 633556노트

반응식

HRID 633556 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH2:17]O)[CH:5]=[N:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[F:16].[Br:19]P(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[Br:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[F:16])=[N:6][CH:5]=[C:4]([CH2:17][Br:19])[CH:3]=1

참가 물질

5

반응물 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 86721075(5-Bromo-6-(2,4-difluorophenoxy)pyridin-3-yl)methanol

생성물 1

HCID 867210763-Bromo-5-(bromomethyl)-2-(2,4-difluorophenoxy)pyridine수율 86%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of the product from Example 60B (0.73 g, 2.309 mmol) in dichloromethane (11.55 mL) under nitrogen was treated dropwise with tribromophosphine (0.218 mL, 2.309 mmol), stirred for one hour and poured into ice water and the pH was adjusted to pH 9 by addition of solid sodium bicarbonate added portionwise. An emulsion formed that was partially removed by filtration. The aqueous layer was extracted with dichloromethane and the organics were combined, washed with saturated aqueous sodium chloride, dried (anhydrous Na2SO4) filtered, and concentrated to afford the title compound (0.75 g, 86%).

후처리

  1. additionadded portionwise
  2. customAn emulsion formed
  3. customthat was partially removed by filtration
  4. extractionThe aqueous layer was extracted with dichloromethane
  5. washwashed with saturated aqueous sodium chloride
  6. dry with materialdried (anhydrous Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-123677e76dc94c9ea82b3a31ec37ba76
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321764B2

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