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

HRID 1433853ノート

反応式

HRID 1433853 の反応式
[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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 62652Cuprous chloride触媒HCID 178418397HCID 178418397、化合物触媒HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8387e951015b4c6db75044133ccf01bd
出典データセット
uspto-grants-2009_11
特許番号
US07612114B2

反応ノート

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