Hydrochloric Acid → 4-(6-Phenylnaphthalene-2-yl)phenylboronic acid

HRID 1662916ノート

反応式

HRID 1662916 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:14]=3)[CH:9]=2)=[CH:4][CH:3]=1.CCCCCC.C([Li])CCC.[B:35](OC(C)C)([O:40]C(C)C)[O:36]C(C)C.Cl>C1(C)C=CC=CC=1.C1COCC1>[C:18]1([C:13]2[CH:14]=[C:15]3[C:10](=[CH:11][CH:12]=2)[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([B:35]([OH:40])[OH:36])=[CH:3][CH:4]=2)[CH:17]=[CH:16]3)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 21531Triisopropyl borateHCID 575398112-(4-Bromophenyl)-6-phenylnaphthaleneHCID 178418339Butyllithium

生成物 1

HCID 575398474-(6-Phenylnaphthalene-2-yl)phenylboronic acid収率 63%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-60 °C

実験手順

Under an argon gas atmosphere, a mixture of 15.3 g (42.6 mmol) of 2-(4-bromophenyl)-6-phenylnaphthalene and 200 mL of dehydrated THF was cooled down to −60 degrees C., and added with 32.8 mL (51.1 mmol) of hexane solution of 1.56M n-butyllithium in drops while being stirred. Then, the reaction mixture was stirred for two hours at −60 degrees C. 24.0 g (128 mol) of triisopropyl borate was dropped into the reaction solution at −60 degrees C. Subsequently, the reaction mixture was warmed up to room temperature, and stirred for 17 hours. The reaction mixture was cooled down to 0 degree C. to be further added with solution of hydrochloric acid, and then stirred for one hour at room temperature. After the reaction, the reaction mixture was further added with toluene, so that aqueous phase thereof was eliminated. After organic phase thereof was dried with magnesium sulfate, the solvent was distilled away under reduced pressure. By recrystallizing residue by toluene and hexane, 8.7 g of 4-(6-phenylnaphthalene-2-yl) phenylboronic acid was obtained at an yield of 63%.

後処理

  1. stirringThen, the reaction mixture was stirred for two hours at −60 degrees C
  2. temperatureSubsequently, the reaction mixture was warmed up to room temperature
  3. stirringstirred for 17 hours
  4. temperatureThe reaction mixture was cooled down to 0 degree C
  5. stirringstirred for one hour at room temperature
  6. customAfter the reaction
  7. dry with materialAfter organic phase thereof was dried with magnesium sulfate
  8. distillationthe solvent was distilled away under reduced pressure
  9. customBy recrystallizing residue by toluene and hexane

出典と根拠

ORDレコード
ord-f6e07d3117c74c41a6d7e7a2bf104804
出典データセット
uspto-grants-2011_10
特許番号
US08034256B2

反応ノート

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