Benzyl Bromide → 3-(Benzyloxy)-5-bromo-2-chloropyridine

HRID 625937노트

반응식

HRID 625937 반응식
[Br:1][C:2]1[CH:3]=[C:4]([OH:9])[C:5]([Cl:8])=[N:6][CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C.O>[CH2:16]([O:9][C:4]1[C:5]([Cl:8])=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

6

반응물 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 167481065-Bromo-2-chloropyridin-3-ol

생성물 1

HCID 226075323-(Benzyloxy)-5-bromo-2-chloropyridine수율 94.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

5-Bromo-2-chloro-pyridin-3-ol (500 mg, 2.399 mmol) and Cs2CO3 (1.2 g, 3.68 mmol) were combined in DMF (10 mL) at RT. To this was added benzyl bromide (0.34 mL, 2.86 mmol). After stirring overnight the mixture was diluted with H2O and extracted with Et2O (3×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated. Flash column (Biotage-SNAP-50 g, 0-10% EtOAc/hexanes) gave the title compound (674 mg, 94%) as a white solid. 1H NMR (500 MHz, CDCl3): δ 8.07 (d, J=2.0 Hz, 1 H); 7.53-7.35 (m, 6 H); 5.16 (s, 2 H). LC/MS (M+H)+ 298/300/302.

후처리

  1. extractionextracted with Et2O (3×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9fc30344cf3f4bb4898d832b3a15b407
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309199B2

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