Trimethyl borate → 7-Borono12,12-dimethyl-10-phenyl-10,12-dihydro-10-aza-indeno[2,1-b]fluorene

HRID 634551ノート

反応式

HRID 634551 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:10]1[CH:9]=[C:8]3[C:21]([CH3:29])([CH3:28])[C:22]4[C:27]([C:7]3=[CH:6][C:5]2=1)=[CH:26][CH:25]=[CH:24][CH:23]=4.[Li]CCCC.[B:35](OC)([O:38]C)[O:36]C>C1COCC1>[B:35]([C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:10]1[CH:9]=[C:8]3[C:21]([CH3:29])([CH3:28])[C:22]4[C:27]([C:7]3=[CH:6][C:5]2=1)=[CH:26][CH:25]=[CH:24][CH:23]=4)([OH:38])[OH:36]

参加物

5

反応物 3

HCID 8470Trimethyl borateHCID 667976632-Bromo-7,7-dimethyl-5-phenyl-5,7-dihydroindeno[2,1-b]carbazoleHCID 178418339Butyllithium

生成物 1

HCID 866960867-Borono12,12-dimethyl-10-phenyl-10,12-dihydro-10-aza-indeno[2,1-b]fluorene収率 82%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

22.3 g (51 mmol) of 7-bromo-12,12-dimethyl-10-phenyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene 12 are dissolved in 600 ml of dry THF and cooled to −78° C. At this temperature, 26.2 ml (65.7 mmol/2.5 M in hexane) of n-BuLi are added over the course of about 5 min., and the mixture is subsequently stirred at −78° C. for a further 2.5 h. At this temperature, 7.3 ml (65.7 mmol) of trimethyl borate are added as rapidly as possible, and the reaction is allowed to come slowly to RT (about 18 h). The reaction solution is washed with water, and the precipitated solid and the organic phase are dried azeotropically with toluene. The crude product is washed by stir-ring with toluene/methylene chloride at about 40° C. and filtered off with suction, giving 16 g (82%) of the product as white solid.

後処理

  1. customto come slowly to RT
  2. custom(about 18 h)
  3. washThe reaction solution is washed with water
  4. dry with materialthe precipitated solid and the organic phase are dried azeotropically with toluene
  5. washThe crude product is washed
  6. stirringby stir-ring with toluene/methylene chloride at about 40° C.
  7. filtrationfiltered off with suction

出典と根拠

ORDレコード
ord-7bdbaf7d7a7847078fcf5b16aa8daaeb
出典データセット
uspto-grants-2016_04
特許番号
US09324954B2

反応ノート

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