Hydrochloric Acid → 9-(dibenzo[b,d]thiophen-4-yl)-9H-carbazol-3-ylboronic acid

HRID 1753712노트

반응식

HRID 1753712 반응식
[Li]CCCC.CCCCCC.Br[C:13]1[CH:14]=[CH:15][C:16]2[N:17]([C:26]3[C:31]4[S:32][C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=5[C:30]=4[CH:29]=[CH:28][CH:27]=3)[C:18]3[C:23]([C:24]=2[CH:25]=1)=[CH:22][CH:21]=[CH:20][CH:19]=3.C[O:40][B:41](OC)[O:42]C.Cl>O1CCCC1>[CH:29]1[C:30]2[C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=3[S:32][C:31]=2[C:26]([N:17]2[C:16]3[CH:15]=[CH:14][C:13]([B:41]([OH:42])[OH:40])=[CH:25][C:24]=3[C:23]3[C:18]2=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:27][CH:28]=1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 8470Trimethyl borateHCID 584795943-bromo-9-(dibenzo[b,d]thiophen-4-yl)-9H-carbazoleHCID 178418339Butyllithium

생성물 1

HCID 903429479-(dibenzo[b,d]thiophen-4-yl)-9H-carbazol-3-ylboronic acid수율 59%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

An excess of 1.6M n-BuLi in hexane (14 mL, 22.3 mmol) was added to a solution of 3-bromo-9-(diberizo[b,d]thiophen-4-yl)-9H-carbazole (8.7 g, 20.3 mmol) in 100 ml dry tetrahydrofuran at −78° C. under N2. The reaction mixture was then maintained at 0° C. for 1 h before cooling to −78° C. Trimethylborate (2.8 g, 26.4 mmol) was added dropwise; the solution was then warmed slowly to room temperature and stirred for 24 h. 2N HCl (50 ml) was added and then the mixture was stirred for a further 1 h. The reaction mixture was extracted with ethyl acetate and water, dried with anhydrous magnesium sulfate, the solvent was evaporated in vacuum, and the residue was crystallized from n-hexane to give the 9-(dibenzo[b,d]thiophen-4-yl)-9H-carbazol-3-ylboronic acid 4.7 g (59%)

후처리

  1. temperaturebefore cooling to −78° C
  2. temperaturethe solution was then warmed slowly to room temperature
  3. stirringthe mixture was stirred for a further 1 h
  4. extractionThe reaction mixture was extracted with ethyl acetate and water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customthe solvent was evaporated in vacuum
  7. customthe residue was crystallized from n-hexane

출처 및 근거

ORD 기록
ord-985c438dc6124981a14bb6d0281246b1
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09166177B2

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