Hydrochloric Acid → (4-Formylthiophen-3-yl)boronic acid

HRID 1714042

반응식

HRID 1714042 반응식
[B:1](OC(C)C)([O:6]C(C)C)[O:2]C(C)C.Br[C:15]1[C:16]([CH:20]2[O:24]CCO2)=[CH:17][S:18][CH:19]=1.[Li]CCCC.Cl>C1(C)C=CC=CC=1.C1COCC1>[CH:20]([C:16]1[C:15]([B:1]([OH:6])[OH:2])=[CH:19][S:18][CH:17]=1)=[O:24]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 12284898HCID 12284898, 화합물HCID 178418339Butyllithium

생성물 1

HCID 4190637(4-Formylthiophen-3-yl)boronic acid수율 95%

시약·촉매·용매 1

HCID 22635083Tetrahydrofuran toluene용매2회

반응 조건

온도
-78 °C

실험 절차

To a 0.5M solution of B(Oi-Pr)3 (1.2 eq) in toluene/THF 4:1 was added a solution of 2-(4-bromo-3-thienyl)-1,3-dioxolane in toluene/THF 4:1, and the mixture was then cooled to −78° C. BuLi (1.5M in hexanes; 1.2 eq) was then added over 1 h, and the solution kept at this temperature for an additional h, then allowed to warm to −20° C. over 3 h; aq 1N HCl was added and the mixture stirred for an additional h at this temperature. Removal of volatiles gave an aqueous solution that was extracted with DCM; the combined organic phases were then washed with brine, dried over Na2SO4 and concentrated in vacuo. Yield: 95%.

후처리

  1. temperatureto warm to −20° C. over 3 h
  2. customRemoval of volatiles
  3. customgave an aqueous solution that
  4. extractionwas extracted with DCM
  5. washthe combined organic phases were then washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-a0f53afc9c454528be29c1e7c46f6753
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795247B2

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