Hydrochloric Acid → 2-Nitro-4-((trifluoromethyl)sulfonyl)phenol

HRID 1968974Notes

Reaction equation

HRID 1968974 reaction equation
[OH-:1].[Na+].Cl[C:4]1[CH:9]=[CH:8][C:7]([S:10]([C:13]([F:16])([F:15])[F:14])(=[O:12])=[O:11])=[CH:6][C:5]=1[N+:17]([O-:19])=[O:18].CO.Cl>O.C(Cl)Cl>[N+:17]([C:5]1[CH:6]=[C:7]([S:10]([C:13]([F:16])([F:15])[F:14])(=[O:12])=[O:11])[CH:8]=[CH:9][C:4]=1[OH:1])([O-:19])=[O:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 15479561-Chloro-2-nitro-4-trifluoromethanesulfonylbenzene

Product 1

HCID 50351872-Nitro-4-((trifluoromethyl)sulfonyl)phenolYield 25.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

Sodium hydroxide (211 mg, 5.28 mmol) was added to a suspension of 1-chloro-2-nitro-4-[(trifluoromethyl)sulfonyl]benzene (297 mg, 1.03 mmol) in H2O (5 mL) at rt, followed by methanol (0.5 mL) to solubilise the starting material, and the reaction was heated at 110° C. for 1 h. The mixture was allowed to cool to rt, diluted with H2O (10 mL) and neutralised with 5 M HCl. DCM was added, the 2 layers were partitioned and the aqueous layer was extracted with DCM (2×). The combined organics were dried (Na2SO4) and concentrated by rotary evaporation to give 2-nitro-4-[(trifluoromethyl)sulfonyl]phenol (D82, 70 mg, 25%) as a colourless oil.

Workup

  1. temperatureto cool to rt
  2. customthe 2 layers were partitioned
  3. extractionthe aqueous layer was extracted with DCM (2×)
  4. dry with materialThe combined organics were dried (Na2SO4)
  5. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-1cb5ed129a424bb29431cd0f3f40041f
Source dataset
uspto-grants-2013_04
Patent number
US08426443B2

Reaction notes

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