Methyl iodide → Methyl 4-bromo-3-(tetrahydropyran-2-yloxy)benzoate

HRID 1662339

반응식

HRID 1662339 반응식
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1.Br[C:19]1C=CC(C(O)=O)=CC=1OC1CCCCO1.C(=O)([O-])[O-].[Cs+].[Cs+].IC>CC(C)=O.O>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:19])=[O:7])=[CH:4][C:3]=1[O:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 674295254-Bromo-3-(tetrahydro-2H-pyran-2-yloxy)benzoic acid 4-bromo-3-(tetrahydro-2H-pyran-2-yloxy)benzoic acid

생성물 1

HCID 16747841Methyl 4-bromo-3-(tetrahydropyran-2-yloxy)benzoate수율 100%

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매

실험 절차

To flask containing 26.1 (2.15 g, 7.14 mmol) and cesium carbonate (3.95 g, 12.1 mmol) in acetone (50 mL), was added iodomethane (0.667 mL, 10.7 mmol). The resulting mixture was stirred overnight. The reaction was diluted with water and extracted with EtOAc. The organic layers were washed with brine, dried over Na2SO4, filtered, concentrated, and then purified by combiflash (0 to 20% EtOAc/Hexanes) to provide methyl 26.2 (2.25 g, 99% yield).

후처리

  1. extractionextracted with EtOAc
  2. washThe organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by combiflash (0 to 20% EtOAc/Hexanes)

출처 및 근거

ORD 기록
ord-8bf91a6cce7a4ce999e9addf49610b4a
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030354B2

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