Sodium Azide → 2-Azido-1-(3-methoxyphenyl)ethanone

HRID 2367381Notes

Reaction equation

HRID 2367381 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[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][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=1)=[O:4])=[N+:14]=[N-:15]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 101294Bromomethyl 3-methoxyphenyl ketone

Product 1

HCID 187928632-Azido-1-(3-methoxyphenyl)ethanoneYield 93.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-bromo-1-[3-(methyloxy)phenyl]ethanone (2.4 g, 10.5 mmol) in THF (80 mL) and water (20 mL) was added sodium azide (1.703 g, 26.2 mmol), and the reaction mixture was stirred at room temperature for 60 hours. Water (40 mL) was added, and the aqueous mixture was extracted with EtOAc (3×80 mL). The organics were dried (Na2SO4), filtered, and concentrated under reduced pressure to afford the title compound (1.87 g) as a brown oil. 1H NMR (400 MHz, CDCl3): δ 3.87 (s, 3H), 4.55 (s, 2H), 7.15-7.18 (m, 1H), 7.38-7.42 (m, 1H), 7.44-7.47 (m, 2H).

Workup

  1. extractionthe aqueous mixture was extracted with EtOAc (3×80 mL)
  2. dry with materialThe organics were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bc8ca14323324e94bda8ecfa991325e9
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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