Sodium Azide → 1-Azido-3-(4-fluoro-3-methoxyphenyl)-3-methylbutan-2-one

HRID 1627347Notes

Reaction equation

HRID 1627347 reaction equation
Br[CH2:2][C:3](=[O:16])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([O:14][CH3:15])[CH:8]=1)([CH3:6])[CH3:5].[N-:17]=[N+:18]=[N-:19].[Na+]>CN(C=O)C.O>[N:17]([CH2:2][C:3](=[O:16])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([O:14][CH3:15])[CH:8]=1)([CH3:6])[CH3:5])=[N+:18]=[N-:19]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86662247HCID 86662247, compound

Product 1

HCID 866622461-Azido-3-(4-fluoro-3-methoxyphenyl)-3-methylbutan-2-oneYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-bromo-3-(4-fluoro-3-methoxyphenyl)-3-methylbutan-2-one (125.4 g, 0.44 mol) in DMF (500 mL) was added NaN3 (37.2 g, 0.572 mol) at 0° C., and the mixture was warmed to room temperature over 3 h with stirring. The reaction mixture was diluted with water (2 L) and extracted with EtOAc (1 L×2). Combined extracts were washed with brine, dried over MgSO4, and concentrated to give 1-azido-3-(4-fluoro-3-methoxyphenyl)-3-methylbutan-2-one (99.5 g), which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3): δ 7.07 (m, 1H), 6.79 (m, 2H), 3.92 (s, 3H), 3.78 (s, 2H), 1.53 (s, 6H).

Workup

  1. extractionextracted with EtOAc (1 L×2)
  2. washCombined extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5b3bb0a3fc474c84b174a26cee6bf758
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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