Tert-Butyl nitrite → 3,5-Dibromobenzonitrile

HRID 1613148Notes

Reaction equation

HRID 1613148 reaction equation
C(ON=O)(C)(C)C.N[C:9]1[C:16]([Br:17])=[CH:15][C:12]([C:13]#[N:14])=[CH:11][C:10]=1[Br:18]>CN(C)C=O>[Br:17][C:16]1[CH:15]=[C:12]([CH:11]=[C:10]([Br:18])[CH:9]=1)[C:13]#[N:14]

Participants

4

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 27353144-amino-3,5-dibromobenzonitrile

Product 1

HCID 27976903,5-Dibromobenzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

To a stirred solution of t-butylnitrite (53.5 μL, 0.449 mmoles) in 1 ml sieve dried dimethylformamide at 50° C. under an atmosphere of nitrogen was added a solution of 4-amino-3,5-dibromobenzonitrile (50 mg, 0.179 mmoles) in 1 mL of DMF. The mixture was stirred at 50° C. for 0.5 hour and partitioned between diethyl ether, ice-water, and ammonium chloride. The organic phase was separated, washed with water and brine, dried over anhydrous sodium, filtered, and evaporated.

Workup

  1. custompartitioned between diethyl ether, ice-water, and ammonium chloride
  2. customThe organic phase was separated
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous sodium
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-3866967c63fd4747a70ec510093f8233
Source dataset
uspto-grants-1993_03
Patent number
US05192758

Reaction notes

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