4-Iodoaniline → 1-Azido-4-iodobenzene

HRID 2190312Notes

Reaction equation

HRID 2190312 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.N(OC(C)(C)C)=O.[N:16]([Si](C)(C)C)=[N+:17]=[N-]>CC#N.CCOC(C)=O>[N:8]([C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=1)=[N+:16]=[N-:17]

Participants

6

Reactant 3

HCID 108934-IodoanilineHCID 10906Tert-Butyl nitriteHCID 78378Azidotrimethylsilane

Product 1

HCID 30168361-Azido-4-iodobenzene

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-iodobenzenamine (2.38 g, 10.9 mmol) in MeCN (20 mL) at 0° C. was added tert-butyl nitrite (1.95 mL, 1.69 g, 16.4 mmol) and azidotrimethylsilane (1.70 mL, 1.49 g, 12.9 mmol). The reaction mixture was warmed to room temperature and stirred for 6 h, heated to 40° C. for 18 h, and diluted with EtOAc. The aqueous phase was washed with water (2×), brine (1×), dried over MgSO4, filtered, and concentrated to give 1-azido-4-iodobenzene which was used in the next step without further purification.

Workup

  1. temperatureheated to 40° C. for 18 h
  2. washThe aqueous phase was washed with water (2×), brine (1×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3bde274b3c834be2846dff3fb815eecf
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

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