Hydrochloric Acid → 2,3-Diphenylbenzo[b]furan-6-boronic acid

HRID 1893108ノート

反応式

HRID 1893108 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:7][C:6]=2[CH:22]=1.C([Li])CCC.[B:28](OC)([O:31]C)[O:29]C.Cl>CCCCCC.C1COCC1>[C:16]1([C:8]2[O:7][C:6]3[CH:22]=[C:2]([B:28]([OH:31])[OH:29])[CH:3]=[CH:4][C:5]=3[C:9]=2[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 598665016-Bromo-2,3-diphenylbenzofuranHCID 178418339Butyllithium

生成物 1

HCID 598665102,3-Diphenylbenzo[b]furan-6-boronic acid収率 60%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-40 °C

実験手順

Under an argon atmosphere, 400 mL of anhydrous THF were added to 40.2 g of 6-bromo-2,3-diphenylbenzo[b]furan, and the mixture was stirred at −40° C. During the stirring, 72 mL of a 1.6-M solution of n-butyllithium in hexane were added to the mixture. The reaction solution was stirred for 1 hour while being heated to 0° C. The reaction solution was cooled to −78° C. again, and a solution of 54.0 g (250 mmol) of trimethyl borate in 50 mL of dry THF was dropped to the solution. The reaction solution was stirred at room temperature for 5 hours. 200 mL of 1N hydrochloric acid were added to the reaction solution, and the mixture was stirred for 1 hour. After that, the water layer was removed. The organic layer was dried with magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The resultant solid was washed with toluene, whereby 21.7 g of 2,3-diphenylbenzo[b]furan-6-boronic acid were obtained (60% yield).

後処理

  1. stirringThe reaction solution was stirred for 1 hour
  2. temperaturewhile being heated to 0° C
  3. temperatureThe reaction solution was cooled to −78° C. again
  4. stirringThe reaction solution was stirred at room temperature for 5 hours
  5. stirringthe mixture was stirred for 1 hour
  6. customAfter that, the water layer was removed
  7. dry with materialThe organic layer was dried with magnesium sulfate
  8. customthe solvent was removed by distillation under reduced pressure
  9. washThe resultant solid was washed with toluene

出典と根拠

ORDレコード
ord-9e838d81e1d74c73a26f061d92b09f21
出典データセット
uspto-grants-2013_08
特許番号
US08512875B2

反応ノート

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