Pyridine → 1-{[6-(1,3-Dioxolan-2-yl)pyridin-2-yl]methyl}pyridinium bromide hydrobromide

HRID 1258582노트

반응식

HRID 1258582 반응식
S(Br)([Br:3])=O.[O:5]1[CH2:9][CH2:8][O:7][CH:6]1[C:10]1[N:15]=[C:14]([CH2:16]O)[CH:13]=[CH:12][CH:11]=1.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)Cl>[BrH:3].[Br-:3].[O:7]1[CH2:8][CH2:9][O:5][CH:6]1[C:10]1[N:15]=[C:14]([CH2:16][N+:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:13]=[CH:12][CH:11]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 68176Thionyl bromideHCID 19361733[6-(1,3-Dioxolan-2-yl)pyridin-2-yl]methanol

생성물 1

HCID 671882711-{[6-(1,3-Dioxolan-2-yl)pyridin-2-yl]methyl}pyridinium bromide hydrobromide수율 193.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a stirred solution thionyl bromide (8.36 g, 40.23 mmol, 1 eq.) in 300 ml dry DCM, cooled to 5° C., was added dropwise a solution of [6-(1,3-dioxolan-2-yl)pyridin-2-yl]methanol (8.1 g, 40.23 mmol, 1 eq.) and pyridine (3.18 g, 40.23 mmol, 1 eq.) in 15 ml dry DCM. On complete addition, the cooling bath was removed, the reaction warmed to room temperature and stirred overnight. 150 ml of water and 150 ml of DCM were added and stirring allowed for 2 mins. The organic layer was separated, dried over MgSO4 and concentrated to give 1-{[6-(1,3-dioxolan-2-yl)pyridin-2-yl]methyl}pyridinium bromide hydrobromide (15.7 g, 96% yield) as a white solid.

후처리

  1. additionOn complete addition
  2. customthe cooling bath was removed
  3. addition150 ml of water and 150 ml of DCM were added
  4. stirringstirring
  5. waitallowed for 2 mins
  6. customThe organic layer was separated
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c6d900cf4c1d46c98f0742e95c39f59b
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466176B2

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