Ammonia → 2-Methoxy-6-(4-methoxy-2-nitrophenyl)naphthalene

HRID 1433853노트

반응식

HRID 1433853 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8](Br)[CH:7]=[CH:6]2.C([Sn](CCCC)(CCCC)[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=1[N+:27]([O-:29])=[O:28])CCC.[Cl-].[Li+].N>CS(C)=O.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.[Cu]Cl.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=3[N+:27]([O-:29])=[O:28])[CH:9]=2)[CH:4]=1

참가 물질

9

반응물 4

HCID 222AmmoniaHCID 787862-Bromo-6-methoxynaphthaleneHCID 433294Lithium ChlorideHCID 23087474Tributyl(4-methoxy-2-nitrophenyl)tin

생성물 1

HCID 230875562-Methoxy-6-(4-methoxy-2-nitrophenyl)naphthalene수율 63.2%

시약·촉매·용매 4

HCID 62652Cuprous chloride촉매HCID 178418397HCID 178418397, 화합물촉매HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

The title compound was synthesized by referring to J. Am. Chem. Soc., 1999, 121, 760. A suspension of 6-methoxy-2-bromonaphthalene (500 mg), tributyl(4-methoxy-2-nitrophenyl)tin (1.1 g), tetrakis(triphenylphosphine)palladium(0) (250 mg), copper(I) chloride (1.0 g) and lithium chloride (540 mg) in dimethylsulfoxide (15 ml) was stirred at 60° C. for 5 hours under a nitrogen atmosphere. Ethyl acetate and aqueous ammonia were sequentially added thereto, the solution was filtered through celite pad, extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was washed with a hexane-diethyl ether system to provide the title compound (412 mg).

후처리

  1. customThe title compound was synthesized
  2. filtrationthe solution was filtered through celite pad
  3. extractionextracted with ethyl acetate
  4. washsequentially washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated in vacuo
  7. washThe residue was washed with a hexane-diethyl ether system

출처 및 근거

ORD 기록
ord-8387e951015b4c6db75044133ccf01bd
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612114B2

반응 노트

불러오는 중…