乙醇 → 4-(6-Cyano-2-naphthyloxy)-3-(2-formylphenyl)nitrobenzene

HRID 895713

反应方程式

HRID 895713 反应方程式
Br[C:2]1[CH:3]=[C:4]([N+:21]([O-:23])=[O:22])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:19]#[N:20])[CH:15]=2)[CH:10]=1.[CH:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1B(O)O)=[O:25].C1(C)C=CC=CC=1.C(O)C>C(=O)([O-])[O-].[Na+].[Na+].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.O>[C:19]([C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([O:8][C:7]1[CH:6]=[CH:5][C:4]([N+:21]([O-:23])=[O:22])=[CH:3][C:2]=1[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH:24]=[O:25])[CH:18]=[CH:17]2)#[N:20]

参与物

8

反应物 4

HCID 702乙醇HCID 1140甲苯HCID 2921892-甲酰基苯硼酸HCID 22380923HCID 22380923，化合物

产物 1

HCID 223809674-(6-Cyano-2-naphthyloxy)-3-(2-formylphenyl)nitrobenzene

试剂、催化剂与溶剂 3

HCID 178418397HCID 178418397，化合物催化剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 10340Carbonic acid sodium salt (1:2)溶剂

实验过程

The compound (3-bromo-4-(6-cyano-2-naphthyloxy)nitrobenzene) (1 g) obtained in a previous production example, 2-formylphenyl boronic acid (610 mg) and tetrakis(triphenylphosphine)palladium (0) (150 mg) were heated to reflux and reacted for 6 hours in a mixture of 2 M sodium carbonate aqueous solution (10 ml), toluene (10 ml) and ethanol (10 ml). After cooling to room temperature, water was added and extraction was performed with ethyl acetate. The ethyl acetate layer was washed with saturated saline and dried over magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel chromatography (200 g, hexane:ethyl acetate=4:1) to obtain 880 mg of 4-(6-cyano-2-naphthyloxy)-3-(2-formylphenyl)nitrobenzene.

后处理

  1. temperaturewere heated
  2. temperatureto reflux
  3. extractionextraction
  4. washThe ethyl acetate layer was washed with saturated saline
  5. dry with materialdried over magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customThe residue was purified by silica gel chromatography (200 g, hexane:ethyl acetate=4:1)

来源与证据

ORD记录
ord-00b3f9566f0247e989e5a7f00222f09f
来源数据集
uspto-grants-2005_07
专利号
US06916837B2

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