Hydrochloric Acid → HCID 22627292, compound

HRID 1108711Notes

Reaction equation

HRID 1108711 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:7]=[CH:8][C:9]=1[O:10][S:11]([C:14]([F:17])([F:16])[F:15])(=[O:13])=[O:12])([O-])=O.Cl.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>CO.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:7]=[CH:8][C:9]=1[O:10][S:11]([C:14]([F:17])([F:15])[F:16])(=[O:13])=[O:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 54201810HCID 54201810, compound

Product 1

HCID 22627292HCID 22627292, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

Iron powder (2.5 g) was added to a stirred mixture of methyl 3-nitro-4-trifluoromethanesulfonyloxyphenylacetate (2.97 g) and conc. hydrochloric acid (7.3 ml) in methanol (22 ml) at 0° C. in some small portion. The reaction mixture was stirred at 20° C. for 2 hours, then poured into a mixture of ethyl acetate and saturated sodium bicarbonate. The organic phase was washed with saturated sodium bicarbonate and brine, dried over sodium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:4) to give methyl 3-amino-4-trifluoromethanesulfonyloxyphenylacetate (2.34 g) as colorless crystals.

Workup

  1. washThe organic phase was washed with saturated sodium bicarbonate and brine
  2. dry with materialdried over sodium sulfate
  3. customevaporated in vacuo
  4. customThe residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:4)

Sources & evidence

ORD record
ord-409ac91ad5de4c4ca241989fb495dee8
Source dataset
uspto-grants-2000_05
Patent number
US06069156

Reaction notes

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