Trimethyl borate → 2,8-Diphenyldibenzothiophen-4-boronic acid

HRID 1748937노트

반응식

HRID 1748937 반응식
[C:1]1([C:7]2[CH:25]=[CH:24][C:10]3[S:11][C:12]4[CH:17]=[CH:16][C:15]([C:18]5[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=5)=[CH:14][C:13]=4[C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.C[O:32][B:33](OC)[O:34]C>O1CCCC1>[C:18]1([C:15]2[CH:16]=[C:17]([B:33]([OH:34])[OH:32])[C:12]3[S:11][C:10]4[CH:24]=[CH:25][C:7]([C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)=[CH:8][C:9]=4[C:13]=3[CH:14]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

참가 물질

5

반응물 3

HCID 8470Trimethyl borateHCID 223821962,8-Diphenyl-dibenzo-thiopheneHCID 178418339Butyllithium

생성물 1

HCID 583096712,8-Diphenyldibenzothiophen-4-boronic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

2,8-diphenyldibenzo[b,d]thiophene (6.0) was dissolved in anhydrous tetrahydrofuran (80 mL) under nitrogen atmosphere and the solution was then cooled to −78° C. 20.0 mL of n-butyl lithium (1.6 M solution) was added dropwise into the reaction mixture and continuously stirred to equilibrate to room temperature. The reaction mixture was then cool to −60° C. and trimethyborate (5.67 mL) was added and the reaction was allowed to stir overnight. The reaction was then quenched with 20% aqueous hydrochloric acid, and extracted the organic layer with ethyl acetate; ethyl acetate layer was then washed thoroughly with water and dried over anhydrous sodium sulfate, and was evaporated to dryness to yield 4.5 g of 2,8-diphenyldibenzo[b,d]thiophene-4-boronic acid.

후처리

  1. customto equilibrate to room temperature
  2. temperatureThe reaction mixture was then cool to −60° C.
  3. stirringto stir overnight
  4. customThe reaction was then quenched with 20% aqueous hydrochloric acid
  5. extractionextracted the organic layer with ethyl acetate
  6. washethyl acetate layer was then washed thoroughly with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customwas evaporated to dryness

출처 및 근거

ORD 기록
ord-f70a1012d1bf41b892ee1042b96380c6
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09153787B2

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