Hydrochloric Acid → 2-(9-Phenanthrenyl)naphthalene-6-boronic acid

HRID 1429327ノート

反応式

HRID 1429327 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]1[C:13]3[C:18]([C:19]4C=CC=C[C:24]=4[CH:25]=1)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:6]=[CH:5]2.[CH2:26]([Li])[CH2:27][CH2:28][CH3:29].[B:31](OC(C)C)([O:36]C(C)C)[O:32]C(C)C.Cl>CCCCCC.C(OCC)C.C1(C)C=CC=CC=1>[CH:26]1[C:24]2[CH:25]=[C:12]([C:7]3[CH:6]=[CH:5][C:4]4[C:9](=[CH:10][CH:11]=[C:2]([B:31]([OH:36])[OH:32])[CH:3]=4)[CH:8]=3)[C:13]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:19]=2[CH:29]=[CH:28][CH:27]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 575398276-Bromo-2-(9-phenanthrenyl)naphthaleneHCID 178418339Butyllithium

生成物 1

HCID 575398092-(9-Phenanthrenyl)naphthalene-6-boronic acid収率 58%

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒HCID 8058Hexane溶媒2 回

反応条件

温度
-10 °C

実験手順

In argon atmosphere, a liquid mixture of 9.80 (25.6 mmol) of 6-bromo-2-(9-phenanthrenyl)naphthalene, 100 ml of dry toluene, and 100 ml of dry diethyl ether was cooled to −10° C. and 19.7 ml (30.7 mmol) of a 1.56 M hexane solution of n-butyllithium was added dropwise under stirring. Further, the reaction mixture was stirred at −10° C. for 4 h. The reaction solution was cooled to −60° C., and 14.4 g (76.7 mmol) of triisopropyl borate was added dropwise. The reaction mixture was heated and stirred at room temperature for 16 h. The reaction mixture was added with hydrochloric acid and stirred at room temperature overnight. After the reaction, the reaction mixture was separated into liquid phases, and the organic phase was washed with water. The solvent was removed by distillation under reduced pressure until the mixture was turned to slurry. After adding hexane to the residue, the solid matter was collected by filtration and recrystallized from THF and then from hexane to obtain 5.20 g (yield: 58%) of 2-(9-phenanthrenyl)naphthalene-6-boronic acid.

後処理

  1. stirringFurther, the reaction mixture was stirred at −10° C. for 4 h
  2. temperatureThe reaction solution was cooled to −60° C.
  3. temperatureThe reaction mixture was heated
  4. stirringstirred at room temperature for 16 h
  5. stirringstirred at room temperature overnight
  6. customAfter the reaction
  7. customthe reaction mixture was separated into liquid phases
  8. washthe organic phase was washed with water
  9. customThe solvent was removed by distillation under reduced pressure until the mixture
  10. additionAfter adding hexane to the residue
  11. filtrationthe solid matter was collected by filtration
  12. customrecrystallized from THF

出典と根拠

ORDレコード
ord-93ef9fa87b4140929eabc64321febf6e
出典データセット
uspto-grants-2015_01
特許番号
US08940412B2

反応ノート

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