Sodium Thiosulfate → 2-Amino-4-(trifluoromethoxy)phenol

HRID 2056106Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[C:8]([O:10][C:11]([F:14])([F:13])[F:12])[CH:7]=[CH:6][C:5]=1[OH:15])([O-])=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(O)C.O>[NH2:1][C:4]1[CH:9]=[C:8]([O:10][C:11]([F:12])([F:13])[F:14])[CH:7]=[CH:6][C:5]=1[OH:15]

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 2-nitro-4-(trifluoromethoxy)phenol (2 g, 0.0089 mol) in ethanol (50 mL) and water (25 mL) was added sodium thiosulfate (6.2 g, 0.0356 mol) at room temperature. The heterogeneous mixture was stirred at 80° C. under an atmosphere of nitrogen for 1 hour. The reaction mixture was cooled to room temperature, and ethanol was removed under reduced pressure. The aqueous layer was extracted with ethyl acetate (3×70 mL), and the organic layer was washed with brine and dried under sodium sulfate. The solvent was removed under reduced pressure to give yellow solid of 2-amino-4-(trifluoromethoxy)phenol (0.9 g, 0.005 mol). TLC (methanol/dichloromethane=5:95) Rf 0.29 MS: MH+: 194

Workup

temperatureThe reaction mixture was cooled to room temperature
customethanol was removed under reduced pressure
extractionThe aqueous layer was extracted with ethyl acetate (3×70 mL)
washthe organic layer was washed with brine
customdried under sodium sulfate
customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-396109b6c4e849f59544872c39ac9450
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07332497B2

Reaction notes

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