Hydrochloric Acid → Ethyl 4-azido-2,5-difluoro-3-difluoromethoxybenzoate

HRID 1584809Notes

Reaction equation

HRID 1584809 reaction equation
[F:1][CH:2]([F:18])[O:3][C:4]1[C:5]([F:17])=[C:6]([CH:12]=[C:13]([F:16])[C:14]=1F)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[N-:19]=[N+:20]=[N-:21].[Na+].C(OCC)(=O)C.Cl>CS(C)=O>[N:19]([C:14]1[C:13]([F:16])=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:5]([F:17])[C:4]=1[O:3][CH:2]([F:18])[F:1])=[N+:20]=[N-:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 150237803-(Difluoromethoxy)-2,4,5-trifluorobenzoic acid ethyl ester

Product 1

HCID 21220333Ethyl 4-azido-2,5-difluoro-3-difluoromethoxybenzoate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In 66 ml of dimethyl sulfoxide was dissolved 13.2 g of ethyl 3-difluoromethoxy-2,4,5-trifluorobenzoate, and to this solution was added 7.3 g of sodium azide, after which the resulting mixture was stirred at room temperature for five hours. The reaction mixture was added to a mixed solvent of 150 ml of ethyl acetate and 150 ml of ice water and the pH was adjusted to 2 with 6N hydrochloric acid, after which the organic layer formed was separated, then washed successively with water and a saturated saline solution, and thereafter dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure. The residue obtained was purified by a column chromatography (eluent: n-hexane:ethyl acetate=10:1), to obtain 13.9 g of colorless, oily ethyl 4-azido-2,5-difluoro-3-difluorome-thoxybenzoate.

Workup

  1. customafter which the organic layer formed
  2. customwas separated
  3. washwashed successively with water
  4. dry with materiala saturated saline solution, and thereafter dried over anhydrous magnesium sulfate
  5. customThe solvent was then removed by distillation under reduced pressure
  6. customThe residue obtained
  7. customwas purified by a column chromatography (eluent: n-hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-bda2c384fdd540ffae9ea05847459a1f
Source dataset
uspto-grants-1999_08
Patent number
US05935952

Reaction notes

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