4,4,5,5-Tetramethyl-2-(2-methyl-3-nitrophenyl)-1,3,2-dioxaborolane → 2-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

HRID 1772069노트

반응식

HRID 1772069 반응식
[CH3:1][C:2]1([CH3:19])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-])=O)[C:10]=2[CH3:18])[O:3]1>CO>[CH3:18][C:10]1[C:9]([B:4]2[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:19])([CH3:1])[O:3]2)=[CH:14][CH:13]=[CH:12][C:11]=1[NH2:15]

참가 물질

3

반응물 1

HCID 467388184,4,5,5-Tetramethyl-2-(2-methyl-3-nitrophenyl)-1,3,2-dioxaborolane

생성물 1

HCID 467380052-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline수율 109%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A 500-mL round-bottomed flask equipped with a magnetic stirrer was charged with 4,4,5,5-Tetramethyl-2-(2-methyl-3-nitro-phenyl)-[1,3,2]dioxaborolane 101e (8.44 g; 32.1 mmol) and methanol (150 mL). The reaction flask was twice evacuated and back-filled with argon. 10% Palladium on charcoal (50% wet, 425 mg dry weight) was then added to the solution, and the reaction flask evacuated and back-filled with hydrogen three times. The reaction was then stirred under balloon pressure of hydrogen at room temperature for 13 h. After this time, the flask was twice evacuated and back-filled with argon, then filtered through a pad of Celite 521 and the filtrate concentrated in vacuo. The resulting residue was dried under high vacuum for 1 d to afford a quantitative yield (8.16 g) of 2-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine 101f as a white solid: mp 110-112° C.; MS (ESI+) m/z 234 (M+H).

후처리

  1. customA 500-mL round-bottomed flask equipped with a magnetic stirrer
  2. customThe reaction flask was twice evacuated
  3. additionback-filled with argon
  4. addition10% Palladium on charcoal (50% wet, 425 mg dry weight) was then added to the solution
  5. customthe reaction flask evacuated
  6. additionback-filled with hydrogen three times
  7. customAfter this time, the flask was twice evacuated
  8. additionback-filled with argon
  9. filtrationfiltered through a pad of Celite 521
  10. concentrationthe filtrate concentrated in vacuo
  11. customThe resulting residue was dried under high vacuum for 1 d

출처 및 근거

ORD 기록
ord-4e00e4d661e74d0abade655ebe5522b7
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09249123B2

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