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

HRID 634551노트

반응식

HRID 634551 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7bdbaf7d7a7847078fcf5b16aa8daaeb
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09324954B2

반응 노트

불러오는 중…