Bromomethyl 4-methoxyphenyl ketone → 2-Azido-1-[4-(methyloxy)phenyl]ethanone

HRID 2367363Notes

Reaction equation

HRID 2367363 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=[O:4].[N-:13]=[N+:14]=[N-:15].[Na+]>C1COCC1.O>[N:13]([CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=[O:4])=[N+:14]=[N-:15]

Participants

5

Reactant 2

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 33557Sodium Azide

Product 1

HCID 109978352-Azido-1-[4-(methyloxy)phenyl]ethanoneYield 102.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 2-bromo-1-[4-(methyloxy)phenyl]ethanone (3.5 g, 15.28 mmol) and sodium azide (1.490 g, 22.92 mmol) in THF (40 mL) and water (13.33 mL) was stirred at 25° C. for 2 hours. The mixture was diluted with water (150 mL), and extracted with Et2O (3×100 mL), dried (Na2SO4), filtered, concentrated to afford the title compound (3.0 g) as a pink solid. 1H NMR (400 MHz, DMSO-d6): δ 3.87 (s, 3H), 4.83 (s, 2H), 7.07 (d, 2H), 7.93 (d, 2H).

Workup

  1. extractionextracted with Et2O (3×100 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7cf5d191b2614f4090b01db1a80eabe9
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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