Phosphorus oxychloride → 7-Bromo-1-Chloroisoquinoline

HRID 551273노트

반응식

HRID 551273 반응식
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][NH:8][C:9]2=O)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:15])=O.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[Cl:15])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 112761337-Bromoisoquinolin-1-ol

생성물 1

HCID 65020247-Bromo-1-Chloroisoquinoline수율 61.9%

시약·촉매·용매 1

HCID 6212Chloroform용매

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온도
100 °C

실험 절차

7-Bromo-2H-isoquinolin-1-one (3.0 g, 13.4 mmol), phosphorus oxychloride (8.22 g, 53.6 mmol), and chloroform (25 mL) combined in a sealed tube and heated with stirring at 100° C. for 4 hours. Cooled to ˜60° C., poured into ice water (100 mL), neutralized carefully with saturated aqueous sodium hydrogencarbonate, extracted into methylene chloride and dried over magnesium sulfate. Flash column chromatography on silica gel gave the product as a pale cream solid (2.01 g, 8.3 mmol). 1H NMR (CDCl3) δ 8.51 (d, 1H), 8.30 (d, 1H), 7.82 (dd, 1H), 7.72 (d, 1H), 7.57 (dd, 1H). ESI MS (M+1)+: 242, 244, 246 (Br, Cl).

후처리

  1. temperatureheated
  2. temperatureCooled to ˜60° C.
  3. extractionextracted into methylene chloride
  4. dry with materialdried over magnesium sulfate

출처 및 근거

ORD 기록
ord-2264de8a5346429cb01dc3bcb5f89043
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947684B2

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