Dimethyl Sulfoxide → 1-Bromo-2-methoxynaphthalene

HRID 563453

반응식

HRID 563453 반응식
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:12].[OH-].[K+].[CH3:15]S(C)=O.IC>O>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:12][CH3:15]

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 113161-Bromo-2-naphtholHCID 14797Potassium Hydroxide

생성물 1

HCID 728601-Bromo-2-methoxynaphthalene수율 69%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A 500 mL three-necked round-bottomed flask was charged with 1-bromonaphthalen-2-ol (30.0 g, 134.5 mmol), potassium hydroxide (KOH) (11.3 g, 201.7 mmol) and DMSO (300 mL), and the mixture was stirred under nitrogen atmosphere for 10 minutes, After cooling the mixture by using ice-water bath, iodomethane (28.6 g, 201.7 mmol) was slowly added dropwise thereto. Then, the resultant mixture was stirred under nitrogen atmosphere at ambient temperature for 12 hours, and then at 50° C. for 1 hour. After cooling to ambient temperature, the reaction mixture was mixed with water (500 mL), and extracted with diethyl ether. Organic mixture was washed three times with distilled water, and dried over anhydrous magnesium sulfate (MgSO4). After removing the solvent by using a rotary evaporator, the residue was purified via silica gel column chromatography (eluent: n-hexane) to obtain 1-bromo-2-methoxynaphthalene (22.0 g, yield: 69.0%) as white solid.

후처리

  1. temperatureAfter cooling the mixture
  2. waitat 50° C. for 1 hour
  3. extractionextracted with diethyl ether
  4. washOrganic mixture was washed three times with distilled water
  5. dry with materialdried over anhydrous magnesium sulfate (MgSO4)
  6. customAfter removing the solvent
  7. customa rotary evaporator
  8. customthe residue was purified via silica gel column chromatography (eluent: n-hexane)

출처 및 근거

ORD 기록
ord-5f3bba70d52444a189792b56345d99b6
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067511B2

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