2-Bromo-2'-nitroacetophenone → HCID 22493425, compound

HRID 1816287Notes

Reaction equation

HRID 1816287 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12])=[O:4].[N-:14]=[N+:15]=[N-:16].C([N+](CCCC)(CCCC)CCCC)CCC>C(#N)C>[N:14]([CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12])=[O:4])=[N+:15]=[N-:16]

Participants

4

Reactant 2

HCID 2440252-Bromo-2'-nitroacetophenoneHCID 57432321-Butanaminium, N,N,N-tributyl-, azide

Product 1

HCID 22493425HCID 22493425, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

2-Bromo-2′-nitroacetophenone (2.69 g, 11.0 mmol) in acetonitrile (20 mL) was cooled to 0° C. under nitrogen and treated with tetrabutylammonium azide (3.29 g, 11.6 mmol, TCI America, Portland, Oreg.) in acetonitrile (20 mL) dropwise. After stirring at room temperature for 30 minutes, the solution was poured into ice water (100 mL) and extracted with diethyl ether (3×30 mL). The extracts were combined, dried over magnesium sulfate, and the volatiles were removed by evaporation under reduced pressure to yield 2.19 g of 2-azido-2′-nitroacetophenone.

Workup

  1. extractionextracted with diethyl ether (3×30 mL)
  2. dry with materialdried over magnesium sulfate
  3. customthe volatiles were removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-201709f73b6a4d559fe631af725e637e
Source dataset
uspto-grants-2005_04
Patent number
US06884801B1

Reaction notes

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