Hydrochloric Acid → HCID 67105798、化合物

HRID 239208ノート

反応式

HRID 239208 の反応式
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:5]=[CH:6][CH:7]=1.C([Li])CCC.[B:32](OC)([O:35]C)[O:33]C.Cl>C(OCC)(=O)C.CCCCCC.O1CCCC1>[C:20]1([C:8]2([C:9]3[CH:10]=[C:11]([B:32]([OH:35])[OH:33])[CH:12]=[CH:13][CH:14]=3)[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=3[C:3]3[C:4]2=[CH:5][CH:6]=[CH:7][CH:2]=3)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 582335499-(3-Bromophenyl)-9-phenyl-9H-fluoreneHCID 178418339Butyllithium

生成物 1

HCID 67105798HCID 67105798、化合物収率 92%

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

In a 100 mL three-neck flask was put 1.4 g (3.6 mmol) of 9-(3-bromophenyl)-9-phenyl-9H-fluorene. The air in the flask was replaced with nitrogen. Then, 36.0 mL of tetrahydrofuran was added to the mixture, and the mixture was stirred at 80° C. for 30 minutes. After the stirring, 2.4 mL (4.0 mmol) of a 1.65 mol/L hexane solution of n-butyllithium was dripped with a syringe, followed by stirring at −80° C. for 2 hours. Then, 0.6 mL (4.8 mmol) of trimethyl borate was added, and the mixture was stirred overnight while the temperature thereof was gradually increased from −80° C. to room temperature. After the stirring, an aqueous solution of hydrochloric acid (1 mol/L) was added to this mixture, and it was then stirred at room temperature for 30 minutes. Then, ethyl acetate was added to separate the organic layer and the aqueous layer of this mixture, and the aqueous layer was extracted with ethyl acetate three times. This ethyl acetate layer and the organic layer were combined, washed with saturated brine, and dried with magnesium sulfate. The obtained mixture was gravity filtered so that magnesium sulfate was removed, and the obtained filtrate was concentrated to give a white solid. Recrystallization of the obtained white solid from a mixed solvent of ethyl acetate and hexane gave 1.2 g of a white solid in 90% yield, which was the substance to be produced. The synthesis scheme of this Step 1 is shown in (E18-1) given below.

後処理

  1. customIn a 100 mL three-neck flask was put
  2. stirringby stirring at −80° C. for 2 hours
  3. stirringthe mixture was stirred overnight while the temperature
  4. temperaturethereof was gradually increased from −80° C. to room temperature
  5. stirringwas then stirred at room temperature for 30 minutes
  6. customto separate the organic layer
  7. extractionthe aqueous layer of this mixture, and the aqueous layer was extracted with ethyl acetate three times
  8. washwashed with saturated brine
  9. dry with materialdried with magnesium sulfate
  10. filtrationfiltered so that magnesium sulfate
  11. customwas removed
  12. concentrationthe obtained filtrate was concentrated
  13. customto give a white solid
  14. customRecrystallization of the obtained white solid from a mixed solvent of ethyl acetate and hexane

出典と根拠

ORDレコード
ord-d0078ebdd5fc4bc3818924ca44c4e28c
出典データセット
uspto-grants-2014_02
特許番号
US08642190B2

反応ノート

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