Benzyl Bromide → 3-(Benzyloxy)-2-chloropyridine

HRID 1809639노트

반응식

HRID 1809639 반응식
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC(C)=O>[CH2:16]([O:8][C:7]1[C:2]([Cl:1])=[N:3][CH:4]=[CH:5][CH:6]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 811362-Chloro-3-pyridinol

생성물 1

HCID 8193743-(Benzyloxy)-2-chloropyridine수율 81.2%

시약·촉매·용매 1

HCID 180Acetone용매

반응 조건

온도
50 °C

실험 절차

To a solution of 2-chloropyridin-3-ol (16.3 g, 125 mmol) and K2CO3 (24.3 g, 176 mmol) in acetone (150 ml) was added dropwise (bromomethyl)benzene (17.9 ml, 151 mmol). The mixture was stirred overnight at 50° C. and then concentrated to dryness. Water (100 ml) was added and the mixture extracted with CH2Cl2. The organics were dried over Na2SO4, and concentrated to a crude residue that was dissolved in 20 ml CH2Cl2. Et2O (250 ml) was added and then the solvent was decanted from the residue. The residue was then purified on a silica gel plug by eluting with 25% EtOAc/Hexanes to give 3-(benzyloxy)-2-chloropyridine (22.3 g, 80% yield) as a solid.

후처리

  1. concentrationconcentrated to dryness
  2. additionWater (100 ml) was added
  3. extractionthe mixture extracted with CH2Cl2
  4. dry with materialThe organics were dried over Na2SO4
  5. concentrationconcentrated to a crude residue that
  6. dissolutionwas dissolved in 20 ml CH2Cl2
  7. additionEt2O (250 ml) was added
  8. customthe solvent was decanted from the residue
  9. customThe residue was then purified on a silica gel plug
  10. washby eluting with 25% EtOAc/Hexanes

출처 및 근거

ORD 기록
ord-b11c1bedc03e4aeeb5f9d294ab4ef46b
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362037B2

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