Ethanol → 3-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

HRID 1405076Notes

Reaction equation

HRID 1405076 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][C:12]([N+:15]([O-])=O)=[CH:11][C:10]=2[CH3:18])[O:3]1.[Cl-].[NH4+].CCO>[Zn].C1COCC1>[CH3:18][C:10]1[CH:11]=[C:12]([CH:13]=[CH:14][C:9]=1[B:4]1[O:5][C:6]([CH3:8])([CH3:7])[C:2]([CH3:19])([CH3:1])[O:3]1)[NH2:15]

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 248204924,4,5,5-Tetramethyl-2-(2-methyl-4-nitrophenyl)-1,3,2-dioxaborolane

Product 1

HCID 177502103-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineYield 100%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Intermediate 26A (1 g, 3.80 mmol), ammonium chloride (1.432 g, 26.6 mmol), and zinc (1.491 g, 22.81 mmol) were added to a flask, followed by the addition of EtOH (10.0 mL) and THF (10.0 mL). The reaction mixture was stirred at room temperature for 2 hours and filtered through a pad of CELITE®. The filtrate was concentrated under reduced pressure to yield Intermediate 26 (885 mg, 100% yield). MS (ES): m/z=234.2 [M+H]+.

Workup

  1. filtrationfiltered through a pad of CELITE®
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-de51050d302846bb909eac369cec786f
Source dataset
uspto-grants-2014_12
Patent number
US08916553B2

Reaction notes

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