Diisopropylamine → (4-Carboxybenzo[b]thiophen-2-yl)boronic acid

HRID 250241노트

반응식

HRID 250241 반응식
[Li]CCCC.C(NC(C)C)(C)C.[S:13]1[CH:17]=[CH:16][C:15]2[C:18]([C:22]([OH:24])=[O:23])=[CH:19][CH:20]=[CH:21][C:14]1=2.[B:25](OC(C)C)([O:30]C(C)C)[O:26]C(C)C>C1COCC1>[C:22]([C:18]1[C:15]2[CH:16]=[C:17]([B:25]([OH:30])[OH:26])[S:13][C:14]=2[CH:21]=[CH:20][CH:19]=1)([OH:24])=[O:23]

참가 물질

6

반응물 4

HCID 7912DiisopropylamineHCID 21531Triisopropyl borateHCID 1051638Benzo[b]thiophene-4-carboxylic acidHCID 178418339Butyllithium

생성물 1

HCID 67272237(4-Carboxybenzo[b]thiophen-2-yl)boronic acid수율 96%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-30 °C

실험 절차

A solution of n-BuLi (2.5M in hexane, 1.69 mol, 676 mL) is added slowly at −78° C. to a solution of diisopropylamine (1.69 mol, 236 mL) in 2 L of anhydrous THF. The mixture is stirred for 30 min. A solution of benzo[b]thiophene-4-carboxylic acid (0.8 mol, 143 g) in 2 L of anhydrous THF is added slowly and the mixture is allowed to reach 0° C. The reaction is cooled to −30° C. and the triisopropyl borate (2 mol, 463 mL) is added slowly. The cooling bath is removed and the mixture is allowed to reach room temperature. The reaction is quenched with 1.3 L of concentrated HCl and 1 L of water. The mixture is stirred overnight. The organic solvent is removed under reduced pressure. The precipitate is collected by filtration, washed with water, and dried under vacuum to yield the title compound (170.5 g, 96%). ES/MS m/e 221 (M−1).

후처리

  1. customto reach 0° C
  2. customThe cooling bath is removed
  3. customto reach room temperature
  4. customThe reaction is quenched with 1.3 L of concentrated HCl and 1 L of water
  5. stirringThe mixture is stirred overnight
  6. customThe organic solvent is removed under reduced pressure
  7. filtrationThe precipitate is collected by filtration
  8. washwashed with water
  9. customdried under vacuum

출처 및 근거

ORD 기록
ord-0acf80ccbd0c42a4a68f85c323069aac
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863302B2

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