Hydrochloric Acid → [3-(Naphthalen-2-yl)phenyl]boronic acid

HRID 912392ノート

反応式

HRID 912392 の反応式
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.CCCCCC.C([Li])CCC.[B:29](OC(C)C)([O:34]C(C)C)[O:30]C(C)C.Cl>C1(C)C=CC=CC=1.C1COCC1>[CH:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:16]=[CH:17][C:8]=1[C:4]1[CH:3]=[C:2]([B:29]([OH:34])[OH:30])[CH:7]=[CH:6][CH:5]=1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 21531Triisopropyl borateHCID 230807732-(3-Bromophenyl)naphthaleneHCID 178418339Butyllithium

生成物 1

HCID 45382255[3-(Naphthalen-2-yl)phenyl]boronic acid収率 67.9%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-10 °C

実験手順

Under an argon gas atmosphere, a mixture of 212 g (748 mmol) of 2(3-bromophenyl) naphthalene and 3 L of dehydrated THF was cooled down to −10 degrees C., and added with 600 ml (948 mmol) of hexane solution of 1.6M n-butyllithium in drops while being stirred. Then, the reaction mixture was stirred for two hours at 0 degree C. The reaction solution was further cooled down to −78 degrees C., and added with 450 g (2.39 mol) of triisopropyl borate in drops. Subsequently, the reaction mixture was stirred for 17 hours at room temperature. The reaction mixture was further added with solution of hydrochloric acid to be stirred for one hour at room temperature. The reaction mixture was further added with 3 L of 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 the obtained solid by toluene, 126 g of 3-(2-naphthyl) phenylboronic acid was obtained at an yield of 67%.

後処理

  1. stirringThen, the reaction mixture was stirred for two hours at 0 degree C
  2. temperatureThe reaction solution was further cooled down to −78 degrees C
  3. stirringSubsequently, the reaction mixture was stirred for 17 hours at room temperature
  4. stirringto be stirred for one hour at room temperature
  5. dry with materialAfter organic phase thereof was dried with magnesium sulfate
  6. distillationthe solvent was distilled away under reduced pressure
  7. customBy recrystallizing the obtained solid by toluene

出典と根拠

ORDレコード
ord-13af4ed133344e998a5e121307500be5
出典データセット
uspto-grants-2011_09
特許番号
US08025815B2

反応ノート

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