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 1363486

Reaction equation

HRID 1363486 reaction equation
[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]

Participants

3

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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 (6) (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 (7) as a white solid: mp 110-112° C.; MS (ESI+) m/z 234 (M+H).

Workup

  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

Sources & evidence

ORD record
ord-d6976be46a0c4d22b0e47b69c48a559d
Source dataset
uspto-grants-2011_02
Patent number
US07884108B2

Linked notes

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