Ethanol → 1-(2-Fluorophenyl)-2-methoxynaphthalene

HRID 1912165ノート

反応式

HRID 1912165 の反応式
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:12][CH3:13].[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O.C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.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>[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:12][CH3:13]

参加物

7

反応物 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 728601-Bromo-2-methoxynaphthaleneHCID 27343542-Fluorophenylboronic acid

生成物 1

HCID 679806421-(2-Fluorophenyl)-2-methoxynaphthalene収率 60%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒2 回

実験手順

Into a 500 mL three-neck flask were placed 8.7 g (35 mmol) of 1-bromo-2-methoxynaphthalene, and 5.0 g (35 mmol) of 2-fluorophenylboronic acid. The air in the flask was replaced with nitrogen. To this mixture were added 120 mL of toluene, 60 mL of ethanol, and 40 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 2.0 g (1.7 mmol) of tetrakis(triphenylphosphine)palladium(0), and the mixture was stirred at 80° C. for 8 hours under a nitrogen stream. The aqueous layer of the obtained 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 over magnesium sulfate, and this mixture was gravity-filtered. An oily substance obtained by concentration of the obtained filtrate was dissolved in about 30 mL of toluene. This solution was suction-filtered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina, and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135). An oily substance obtained by concentration of the obtained filtrate was dried under reduced pressure, so that 5.3 g of a pale yellow oily substance of the object of the synthesis was obtained in 60% yield. The above-described synthesis scheme is illustrated in the following scheme (C-1).

後処理

  1. customInto a 500 mL three-neck flask were placed
  2. customto be degassed
  3. stirringthe mixture was stirred at 80° C. for 8 hours under a nitrogen stream
  4. extractionThe aqueous layer of the obtained 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 over magnesium sulfate
  8. filtrationthis mixture was gravity-filtered
  9. customAn oily substance obtained by concentration of the obtained filtrate
  10. filtrationThis solution was suction-filtered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina, and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135)
  11. customAn oily substance obtained by concentration of the obtained filtrate
  12. customwas dried under reduced pressure, so that 5.3 g of a pale yellow oily substance of the object of the synthesis
  13. customwas obtained in 60% yield
  14. customThe above-described synthesis scheme

出典と根拠

ORDレコード
ord-c1ef30d96b924dfbb75c1e238de2fa12
出典データセット
uspto-grants-2013_12
特許番号
US08604224B2

反応ノート

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