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

HRID 897910

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-c729e579dfcc42dd94c6bd422027e908
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06921763B2

Linked notes

Loading…