Sodium Hydroxide → Methanesulfonic acid, trifluoro-, 4-aminophenyl ester

HRID 1736499Notes

Reaction equation

HRID 1736499 reaction equation
[F:1][C:2]([F:17])([F:16])[S:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1)(=[O:5])=[O:4].[OH-].[Na+]>C(O)C.Cl>[F:16][C:2]([F:1])([F:17])[S:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1)(=[O:4])=[O:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 5498704-Nitrophenyl trifluoromethanesulfonate

Product 1

HCID 572619Methanesulfonic acid, trifluoro-, 4-aminophenyl ester

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

The 4-(trifluoromethylsulfonyloxy)-1-nitrobenzene (27.1 grams; 0.10 mole) in 300 ml of ethanol was added dropwise to 94.8 grams of stannous chloride (0.5 mol; 5 equivalents) in 525 ml of concentrated HCl, at room temperature. The rate of addition was controlled to prevent the temperature of the reaction mixture from rising. The reaction mixture was stirred for 3 hours, 10N NaOH added until the pH was ~12, and extracted into ether. The ether extract was washed with water, dried over magnesium sulfate, and the ether evaporated to yield the desired 4-(trifluoromethylsulfonyloxy)aniline as a yellowish brown oil. Its identity was confirmed by NMR, MS, and elemental analysis, the last of which showed:

Workup

  1. additionThe rate of addition
  2. extractionextracted into ether
  3. extractionThe ether extract
  4. washwas washed with water
  5. dry with materialdried over magnesium sulfate
  6. customthe ether evaporated

Sources & evidence

ORD record
ord-3d39e100443a4435ba05ce1841f88982
Source dataset
uspto-grants-1996_07
Patent number
US05541224

Reaction notes

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