Dimethyl Sulfate → 5-Bromo-2-chloro-4-methoxybenzonitrile

HRID 46228

반응식

HRID 46228 반응식
[Br:1][C:2]1[C:3]([OH:11])=[CH:4][C:5]([Cl:10])=[C:6]([CH:9]=1)[C:7]#[N:8].S(OC)(O[CH3:16])(=O)=O.O.[OH-].[Li+]>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[C:3]([O:11][CH3:16])=[CH:4][C:5]([Cl:10])=[C:6]([CH:9]=1)[C:7]#[N:8]

참가 물질

6

반응물 3

HCID 6497Dimethyl SulfateHCID 168937Lithium hydroxide, monohydrateHCID 533304525-Bromo-2-chloro-4-hydroxybenzonitrile2회

생성물 1

HCID 672873335-Bromo-2-chloro-4-methoxybenzonitrile수율 76%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 5-bromo-2-chloro-4-hyroxybenzonitrile (compound 87, 38.1 g, 164 mmol), dimethyl sulfate (20.1 mL, 213 mmol), and lithium hydroxide monohydrate (8.93 g, 213 mmol) in THF (500 mL) was refluxed overnight. The mixture was cooled to ambient temperature and then diluted with EtOAc. The EtOAc solution was washed with water and brine prior to drying over anhydrous MgSO4. Filtration and removal of the voletiles under reduced pressure left the crude product which was purified by column chromatography (5-40% EtOAC/hexanes) to yield 5-bromo-2-chloro-4-methoxybenzonitrile (30.7 g, 76%) as a white solid.

후처리

  1. temperaturewas refluxed overnight
  2. washThe EtOAc solution was washed with water and brine
  3. dry with materialto drying over anhydrous MgSO4
  4. filtrationFiltration and removal of the voletiles under reduced pressure
  5. waitleft the crude product which
  6. customwas purified by column chromatography (5-40% EtOAC/hexanes)

출처 및 근거

ORD 기록
ord-d8a489cf90a04a668a483a1680f139a3
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541380B2

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