Water → HCID 58251652、化合物

HRID 37755ノート

反応式

HRID 37755 の反応式
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH3:13])=[CH:4][CH:3]=1.[CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1[C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].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.C1(C)C=CC=CC=1.O1CCCC1>[CH3:13][O:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([C:27]2[CH:26]=[CH:25][C:24]([C:15]3[CH:16]=[CH:17][C:18]4[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:14]=3)=[CH:29][CH:28]=2)=[CH:3][CH:4]=1

参加物

8

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1385211-Bromo-4-methoxynaphthaleneHCID 453822584-(2-Naphthyl)phenylboronic Acid

生成物 1

HCID 58251652HCID 58251652、化合物収率 68.6%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

1-Bromo-4-methoxynaphthalene (25 g, 0.105 mol), 4-(naphthalen-2-yl)phenylboronic acid (30.4 g, 0.137 mol), potassium carbonate (21.9 g, 0.16 mol), tetrakis(triphenylphosphine)palladium(0) (2.4 g, 0.01 mol), water (25 mL), tetrahydrofuran (75 mL) and toluene (75 mL) were stirred in a 250 mL round-bottom flask for 12 hours under reflux. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with ethyl acetate (300 mL) and water (1000 mL). The organic layer was dried with magnesium sulfate and concentrated under reduced pressure. The resulting solid was dissolved in hot toluene (400 mL) and filtered. The filtrate was recrystallized in methanol (800 mL). The resultant solid was filtered and washed with hexane (300 mL) to obtain a product (26 g, 0.072 mol, 68.4%).

後処理

  1. temperatureunder reflux
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate (300 mL) and water (1000 mL)
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe resulting solid was dissolved in hot toluene (400 mL)
  7. filtrationfiltered
  8. customThe filtrate was recrystallized in methanol (800 mL)
  9. filtrationThe resultant solid was filtered
  10. washwashed with hexane (300 mL)

出典と根拠

ORDレコード
ord-a13ff7dac0f443fb964422a0af8d4114
出典データセット
uspto-grants-2013_09
特許番号
US08524381B2

反応ノート

読み込み中…