Water → Ethyl 4-azido-2-fluoro-3-methylbenzoate

HRID 377273Notes

Reaction equation

HRID 377273 reaction equation
[F:1][C:2]1[C:12]([CH3:13])=[C:11](F)[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[N-:15]=[N+:16]=[N-:17].[Na+].C1(C)C=CC=CC=1.O>CS(C)=O>[N:15]([C:11]1[CH:10]=[CH:9][C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:2]([F:1])[C:12]=1[CH3:13])=[N+:16]=[N-:17]

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 33557Sodium AzideHCID 19358331HCID 19358331, compound

Product 1

HCID 19358340Ethyl 4-azido-2-fluoro-3-methylbenzoateYield 42.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In 47 ml of dimethyl sulfoxide was dissolved 4.65 g of ethyl 2,4-difluoro-3-methylbenzoate, followed by adding thereto 3.32 g of sodium azide, and the resulting mixture was stirred at 70° C. for 20 hours. The reaction mixture was cooled to room temperature and then added to a mixed solvent of 150 ml of toluene and 150 ml of water, and the organic layer was separated. The organic layer obtained was washed with water and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent. The resulting residue was purified by a column chromatography (eluent: toluene) to obtain 2.20 g of ethyl 4-azido-2-fluoro-3-methylbenzoate as a light-yellow oil.

Workup

  1. additionby adding
  2. customthe organic layer was separated
  3. customThe organic layer obtained
  4. washwas washed with water
  5. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe resulting residue was purified by a column chromatography (eluent: toluene)

Sources & evidence

ORD record
ord-9a77eb6135e640e58217b98678ef6a41
Source dataset
uspto-grants-2000_02
Patent number
US06025370

Reaction notes

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