Hydrochloric Acid → HCID 59629170、化合物

HRID 1045303ノート

反応式

HRID 1045303 の反応式
Br[C:2]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][C:9](C4C=CC5C(=CC=CC=5)C=4)=[CH:10][CH:11]=3)[CH:6]=[CH:5][C:4]=2[CH:3]=1.[CH3:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].[CH2:32]([Li])[CH2:33][CH2:34][CH3:35].C([O:40][B:41](OC(C)C)[O:42]C(C)C)(C)C.Cl>C1(C)C=CC=CC=1.C1COCC1>[CH:28]1[C:27]2[C:32](=[CH:33][CH:34]=[CH:35][CH:26]=2)[CH:31]=[CH:30][C:29]=1[C:9]1[CH:8]=[C:7]2[C:6]([C:5]3[CH:14]=[CH:15][C:2]([B:41]([OH:42])[OH:40])=[CH:3][C:4]=3[CH:13]=[CH:12]2)=[CH:11][CH:10]=1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 21531Triisopropyl borateHCID 59629216HCID 59629216、化合物HCID 178418339Butyllithium

生成物 1

HCID 59629170HCID 59629170、化合物収率 62%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

Under an argon gas atmosphere, a mixture of 15.0 g (39.1 mmol) of 2-bromo-7-(naphthalene-2-yl)phenanthrene and 150 mL of dehydrated THF was cooled down to minus 60 degree C. Then, 30.3 ml (46.7 mmol) of hexane solution of 1.55M n-butyllithium was dropped into the mixture while the mixture was being stirred. The reaction mixture was further stirred at minus 60 degrees for 2 hours. The reaction solution was again cooled down to minus 70 degrees C., and 22.08 g (117.4 mmol) of triisopropylborate was dropped into the solution. The reaction mixture was warmed back to room temperature, stirred for 2 hours and left unattended for one night. Subsequently, the reaction mixture was added with aqueous solution of hydrochloric acid while being cooled on an ice bath, and stirred for 1 hour at room temperature. The reaction mixture was added with toluene, and aqueous phase thereof was eliminated. After organic phase thereof was dried with magnesium sulfate, the solvent was distilled away under reduced pressure. By recrystallizing the obtained solid with toluene-hexane, 8.4 g of 7-(naphthalene-2-yl)phenanthrene-2-ylboronic acid was obtained at an yield of 62%.

後処理

  1. temperaturewas cooled down to minus 60 degree C
  2. stirringThe reaction mixture was further stirred at minus 60 degrees for 2 hours
  3. temperatureThe reaction mixture was warmed back to room temperature
  4. stirringstirred for 2 hours
  5. waitleft
  6. waitunattended for one night
  7. temperaturewhile being cooled on an ice bath
  8. stirringstirred for 1 hour at room temperature
  9. dry with materialAfter organic phase thereof was dried with magnesium sulfate
  10. distillationthe solvent was distilled away under reduced pressure
  11. customBy recrystallizing the obtained solid with toluene-hexane

出典と根拠

ORDレコード
ord-7e398159eab74cbb848a2002d47c7eb1
出典データセット
uspto-grants-2013_10
特許番号
US08568903B2

反応ノート

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