Dimethyl Sulfate → 5-Bromo-2-chloro-3,4-dimethoxybenzaldehyde

HRID 2206755노트

반응식

HRID 2206755 반응식
[Br:1][C:2]1[C:3]([OH:13])=[C:4]([O:11][CH3:12])[C:5]([Cl:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH3:14]OS(OC)(=O)=O>C1COCC1>[Br:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([O:11][CH3:12])[C:5]([Cl:10])=[C:6]([CH:9]=1)[CH:7]=[O:8]

참가 물질

4

반응물 2

HCID 6497Dimethyl SulfateHCID 867140745-Bromo-2-chloro-4-hydroxy-3-methoxybenzaldehyde

생성물 1

HCID 867140735-Bromo-2-chloro-3,4-dimethoxybenzaldehyde수율 70.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
65 °C

실험 절차

To the mixture of aldehyde 156 (15.0 g, 56.5 mmol) in THF (300 mL) were added dimethylsulfate (7.0 mL, 73.5 mmol) and LiOH monohydrate (3.1 g, 73.5 mmol). The mixture was stirred for 3 hours at 65° C. The mixture was cooled to r.t. and filtered to remove insoluble materials through celite. The filtrate was extracted with EtOAc/aq. 50% NaCl solution (200 mL/500 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the compound 157 (11.1 g, 70%).

후처리

  1. temperatureThe mixture was cooled to r.t.
  2. filtrationfiltered
  3. customto remove insoluble materials through celite
  4. extractionThe filtrate was extracted with EtOAc/aq
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-bfc1486d0cc84611b8114257e06186b8
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09371303B2

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