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

HRID 1662911ノート

反応式

HRID 1662911 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.CCCCCC.[CH2:32]([Li])[CH2:33][CH2:34][CH3:35].[B:37](OC(C)C)([O:42]C(C)C)[O:38]C(C)C.Cl>C(OCC)C.C1(C)C=CC=CC=1>[CH:32]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:37]([OH:42])[OH:38])[CH:3]=4)[CH:8]=3)[C:13]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:19]=2[CH:35]=[CH:34][CH:33]=1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 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 2

HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
-10 °C

実験手順

Under an argon gas atmosphere, a mixture of 9.80 g (25.6 mmol) of 6-bromo-2-(9-phenanthrenyl)naphthalene, 100 mL of dehydrated toluene and 100 mL of dehydrated diethylether was cooled down to −10 degrees C., and added with 19.7 mL (30.7 mmol) of hexane solution of 1.56M n-butyllithium in drops while being stirred. Then, the reaction mixture was stirred for four hours at −10 degree C. The reaction mixture was further cooled down to −60 degrees C., and added with 14.4 g (76.7 mmol) of triisopropyl borate in drops. The reaction mixture was subsequently warmed up to room temperature, and stirred for 16 hours at room temperature. The reaction mixture was further added with solution of hydrochloric acid to be stirred for one night at room temperature. After the reaction, the reaction mixture experienced liquid separation, organic phase thereof was cleansed with water, and the solvent was distilled away under reduced pressure until the reaction mixture became slurry. By adding residue thereof with hexane, filtering the solid and recrystallizing the residue by THF and hexane, 5.20 g of 2-(9-phenanthrenyl)naphthalene-6-boronic acid was obtained at an yield of 58%.

後処理

  1. stirringThen, the reaction mixture was stirred for four hours at −10 degree C
  2. temperatureThe reaction mixture was further cooled down to −60 degrees C
  3. temperatureThe reaction mixture was subsequently warmed up to room temperature
  4. stirringstirred for 16 hours at room temperature
  5. stirringto be stirred for one night at room temperature
  6. customAfter the reaction
  7. customliquid separation, organic phase
  8. distillationthe solvent was distilled away under reduced pressure until the reaction mixture
  9. additionBy adding residue
  10. filtrationwith hexane, filtering the solid
  11. customrecrystallizing the residue by THF and hexane

出典と根拠

ORDレコード
ord-c5d9b747bcbc44138bcb20e6188205b6
出典データセット
uspto-grants-2011_10
特許番号
US08034256B2

反応ノート

読み込み中…