4-Bromophenacyl bromide → 2-azido-1-(4-bromophenyl)ethanone

HRID 1943574Notes

Reaction equation

HRID 1943574 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1)=[O:4].[N-:12]=[N+:13]=[N-:14].[Na+]>CO>[N:12]([CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1)=[O:4])=[N+:13]=[N-:14]

Participants

4

Reactant 2

HCID 74544-Bromophenacyl bromideHCID 33557Sodium Azide

Product 1

HCID 110210042-azido-1-(4-bromophenyl)ethanoneYield 83.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2,4′-dibromoacetophenone (1.390 g, 5.0 mmol) in MeOH (10 mL) was poured over 10 mL of an aqueous solution of sodium azide (0.325 g, 5.00 mmol) in an ice bath. The mixture was stirred at room temperature for 18 hours. The solvent was removed and then extracted with ethyl ether (20 mL) and water (20 mL). The organic layer was dried over MgSO4 and concentrated in vacuo to obtain 2-azido 4′-bromoacetophenone (1.0 g, 4.17 mmol, 83% yield). 1H NMR (CDCl3) 5.45 (s, 2H), 7.67 (d, J=8.4 Hz, 2H), 7.79 (d, J=8.4 Hz, 2H) ppm.

Workup

  1. customThe solvent was removed
  2. extractionextracted with ethyl ether (20 mL) and water (20 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c913f17f6b9e443bada90e6eade854b3
Source dataset
uspto-grants-2013_03
Patent number
US08394742B2

Reaction notes

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