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 1772069ノート

反応式

HRID 1772069 の反応式
[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]

参加物

3

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4e00e4d661e74d0abade655ebe5522b7
出典データセット
uspto-grants-2016_02
特許番号
US09249123B2

反応ノート

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