Sodium Carbonate → 1-(3-Methoxyphenyl)-2-methyl-4-nitrobenzene

HRID 1700993노트

반응식

HRID 1700993 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH3:11].[CH3:12][O:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:12][O:13][C:14]1[CH:19]=[C:18]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=2[CH3:11])[CH:17]=[CH:16][CH:15]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 2516721-Bromo-2-methyl-4-nitrobenzeneHCID 2734370(3-Methoxyphenyl)boronic acid

생성물 1

HCID 183192671-(3-Methoxyphenyl)-2-methyl-4-nitrobenzene수율 90.1%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 80711,2-Dimethoxyethane용매

실험 절차

A solution of 2-bromo-5-nitrotoluene (40.0 gm, 185 mmol) in 1,2-dimethoxyethane (600 mL) was added to tetrakis(triphenylphosphine)palladium(0) (9.77 gm, 9.25 mmol) under nitrogen at room temperature. A solution of 3-methoxyphenylboronic acid (31.5 gm, 207 mmol) in ethanol (150 mL) was added. Finally, 2M aqueous sodium carbonate (800 mL) was added and the mixture was heated under reflux with rapid mechanical stirring for 18 h. After being cooled, the mixture was partitioned between ethyl acetate and water and the organic phase was dried (Na2SO4) and concentrated under reduced pressure. Purification by column chromatography on silica gel eluting with hexane:ethyl acetate=98:2 then 95:5 gave 1-(3-methoxyphenyl)-2-methyl-4-nitrobenzene (40.55 gm, 90%).

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux with rapid
  3. temperatureAfter being cooled
  4. customthe mixture was partitioned between ethyl acetate and water
  5. dry with materialthe organic phase was dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customPurification by column chromatography on silica gel eluting with hexane

출처 및 근거

ORD 기록
ord-fc0c661dc72c4bb9ab3fab391cb08d6c
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06350907B1

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