Toluene → 6-Phenylnaphtho[2,1-b]benzofuran

HRID 1189604ノート

反応式

HRID 1189604 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:8]1[C:24]2[C:16]3[C:17]4[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=4[O:19][C:15]=3[C:14](B(O)O)=[CH:13][C:12]=2[CH:11]=[CH:10][CH:9]=1.C1(C)C=CC=CC=1.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.C(O)C>[C:2]1([C:14]2[C:15]3[O:19][C:18]4[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=4[C:16]=3[C:24]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[CH:13]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 1140TolueneHCID 7961BromobenzeneHCID 10340Sodium CarbonateHCID 67980539Naphtho[2,1-b]benzofuran-6-ylboronic acid

生成物 1

HCID 679804546-Phenylnaphtho[2,1-b]benzofuran収率 56%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒

実験手順

Into a 200 mL three-neck flask were placed 0.90 g (5.7 mmol) of bromobenzene and 1.5 g (5.7 mol) of benzo[b]naphtho[1,2-d]furan-6-boronic acid, and the air in the flask was replaced with nitrogen. To this mixture were added 20 mL of toluene, 10 mL of ethanol, and 6.0 mL of an aqueous solution of sodium carbonate (2.0 mol/L). While the pressure was reduced, this mixture was stirred to be degassed. To this mixture was added 0.33 g (0.28 mmol) of tetrakis(triphenylphosphine)palladium(0), and the mixture was stirred at 80° C. for 2 hours under a nitrogen stream. After that, the aqueous layer of this mixture was subjected to extraction with toluene, and the obtained solution of the extract and the organic layer were combined and washed with saturated brine. The organic layer was dried with magnesium sulfate, and this mixture was gravity-filtered. An oily substance obtained by concentration of the obtained filtrate was purified by silica gel column chromatography (a developing solvent in which the ratio of hexane to toluene was 19:1) to give a white solid. The obtained solid was recrystallized with a mixed solvent of toluene and hexane, so that 0.95 g of white needle-like crystals of the object of the synthesis were obtained in 56% yield. The reaction scheme is illustrated in (R-1).

後処理

  1. customInto a 200 mL three-neck flask were placed
  2. customto be degassed
  3. stirringthe mixture was stirred at 80° C. for 2 hours under a nitrogen stream
  4. extractionAfter that, the aqueous layer of this mixture was subjected to extraction with toluene
  5. extractionthe obtained solution of the extract
  6. washwashed with saturated brine
  7. dry with materialThe organic layer was dried with magnesium sulfate
  8. filtrationthis mixture was gravity-filtered
  9. customAn oily substance obtained by concentration of the obtained filtrate
  10. customwas purified by silica gel column chromatography (a developing solvent in which the ratio of hexane to toluene
  11. customto give a white solid
  12. customThe obtained solid was recrystallized with a mixed solvent of toluene and hexane, so that 0.95 g of white needle-like crystals of the object of the synthesis
  13. customwere obtained in 56% yield
  14. customThe reaction scheme

出典と根拠

ORDレコード
ord-841ace94b30e47e39a3223fae244b69a
出典データセット
uspto-grants-2014_03
特許番号
US08674117B2

反応ノート

読み込み中…