Toluene → 9-([2,2'-Binaphthalen]-7-yl)-10-(naphthalen-1-yl)anthracene

HRID 2179850ノート

反応式

HRID 2179850 の反応式
FC(F)(F)S(OC1C=CC2C(=CC([C:17]3[C:18]4[C:23]([C:24]([C:31]5[C:40]6[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=6)[CH:34]=[CH:33][CH:32]=5)=[C:25]5[C:30]=3[CH:29]=[CH:28][CH:27]=[CH:26]5)=[CH:22][CH:21]=[CH:20][CH:19]=4)=CC=2)C=1)(=O)=O.[CH:43]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH:46]=[CH:45][C:44]=1B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C:64]1([CH3:70])[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1.Cl[C:72]1[CH:77]=CC=C[CH:73]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.CO.O.C(O)C>[CH:43]1[C:52]2[C:47](=[CH:48][CH:49]=[C:50]([C:17]3[C:30]4[C:25]([C:24]([C:31]5[C:40]6[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=6)[CH:34]=[CH:33][CH:32]=5)=[C:23]5[C:18]=3[CH:19]=[CH:20][CH:21]=[CH:22]5)=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:51]=2)[CH:46]=[CH:45][C:44]=1[C:66]1[CH:67]=[CH:68][C:69]2[C:64](=[CH:70][CH:73]=[CH:72][CH:77]=2)[CH:65]=1

参加物

11

反応物 5

HCID 1140TolueneHCID 7964ChlorobenzeneHCID 62657Potassium Phosphate, TribasicHCID 2734375(Naphthalen-2-yl)boronic acidHCID 867013487-(10-(Naphthalen-1-yl)anthracen-9-yl)naphthalen-2-yl trifluoromethane sulfonate

生成物 1

HCID 1232150859-([2,2'-Binaphthalen]-7-yl)-10-(naphthalen-1-yl)anthracene

試薬・触媒・溶媒 5

HCID 75806Tricyclohexylphosphine触媒HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒HCID 702Ethanol溶媒HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

Under the nitrogen atmosphere, 7-(10-(naphthalen-1-yl) anthracen-9-yl)naphthalen-2-yl trifluoromethane sulfonate (3.0 g) as the fifth intermediate compound, 2-naphthalene boronic acid (1.0 g), (Pd(dba)2) (0.03 g), tricyclohexyl phosphine (0.03 g), potassium phosphate (2.2 g) and a mixture solvent (22 ml) of toluene, ethanol and water (toluene/ethanol/water=9/1/1 (volume ratio)) were added to a flask and refluxed for 3 hours. Once the heating is completed, the reaction solution was cooled to room temperature and added with methanol. The precipitates were collected by suction filtration. The obtained solid was washed with water followed by methanol, and washed further with ethyl acetate. The obtained crude product was dissolved in chlorobenzene, and colored components were removed by passing through a silica gel short column. After re-crystallization with chlorobenzene, 9-([2,2′-binaphthalen]-7-yl)-10-(naphthalen-1-yl)anthracene (1.5 g) was obtained as the target compound represented by Formula (1-34). The scheme is shown in the following “Reaction 8”.

後処理

  1. temperaturerefluxed for 3 hours
  2. filtrationThe precipitates were collected by suction filtration
  3. washThe obtained solid was washed with water
  4. washwashed further with ethyl acetate
  5. customThe obtained crude product
  6. customcolored components were removed
  7. customAfter re-crystallization with chlorobenzene

出典と根拠

ORDレコード
ord-8ad5102b8bf34e319afe906b6d5b2044
出典データセット
uspto-grants-2015_06
特許番号
US09070885B2

反応ノート

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