Diisopropylethylamine → 5-Tert-butyl-2-methoxy-3-nitrobenzonitrile

HRID 1181926Notes

Reaction equation

HRID 1181926 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([N+:14]([O-:16])=[O:15])[C:8]([OH:13])=[C:9]([CH:12]=1)[C:10]#[N:11])([CH3:4])([CH3:3])[CH3:2].[CH:17](N(CC)C(C)C)(C)C.C[Si](C=[N+]=[N-])(C)C>CO.C(#N)C>[C:1]([C:5]1[CH:6]=[C:7]([N+:14]([O-:16])=[O:15])[C:8]([O:13][CH3:17])=[C:9]([CH:12]=1)[C:10]#[N:11])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 167693TrimethylsilyldiazomethaneHCID 589806535-Tert-butyl-2-hydroxyl-3-nitro-benzonitrile

Product 1

HCID 508831995-Tert-butyl-2-methoxy-3-nitrobenzonitrileYield 99.9%

Reagents, catalysts & solvents 1

HCID 21959252Acetonitrile methanolSolvent

Procedure

The above nitrile (0.5 g, 2.27 mmol) was taken up in 1:9 methanol/acetonitrile (20 mL). N,N-diisopropylethylamine (1.1 mL, 6.35 mmol) was added dropwise followed by (trimethylsilyl)diazomethane (3.2 mL, 6.35 mmol). The reaction was stirred until the bubbling stopped (20 min) and the reaction was quenched with water. The water was extracted 3× with methylene chloride, dried over Na2SO4, filtered, and concentrated in vacuo to give 5-tert-butyl-2-methoxy-3-nitro-benzonitrile (0.531 g, 99%) as a yellow solid.

Workup

  1. custom(20 min)
  2. customthe reaction was quenched with water
  3. extractionThe water was extracted 3× with methylene chloride
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eaae38b0452b44629a10b48db7c58303
Source dataset
uspto-grants-2007_10
Patent number
US07285545B2

Reaction notes

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