Trifluoroacetic acid → Ethyl {[5-(methyloxy)-2-nitro-4-(trifluoromethyl)phenyl]oxy}acetate

HRID 2114396Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:4]([C:13]([F:16])([F:15])[F:14])=[CH:5][C:6]([N+:10]([O-:12])=[O:11])=[C:7]([OH:9])[CH:8]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].FC(F)(F)C(O)=O>CN(C)C=O.C(OCC)(=O)C.CC#N.O>[CH3:1][O:2][C:3]1[C:4]([C:13]([F:14])([F:15])[F:16])=[CH:5][C:6]([N+:10]([O-:12])=[O:11])=[C:7]([O:9][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

5-(methyloxy)-2-nitro-4-(trifluoromethyl)phenol (0.5 g, 2.1 mmol) was dissolved in 1 mL of dimethylformamide under argon. Potassium carbonate was added and the mixture was allowed to stir for 5 minutes before ethyl bromoacetate (2.3 mL, 21.0 mmol) was slowly delivered to the flask. The mixture was warmed to 80° C. and maintained at that temperature for one hour. The reaction was determined to be complete by LCMS (two Aquasil C18, 20×1 mm columns were run in sequence, 4 minutes at 0.1 mL/min, 1-99% CH3CN/H2O with 0.018% trifluoroacetic acid, ES) Rt=2.1 min and m/e 324 [M+1]+. The mixture was allowed to cool to room temperature before it was diluted with 50 mL of ethyl acetate. The organic layer was washed with water (3×20 mL) and brine (3×20 mL). The organic phase was dried over Na2SO4, filtered and concentrated to give ethyl {[5-(methyloxy)-2-nitro-4-(trifluoromethyl)phenyl]oxy}acetate (0.71 g, 2.2 mmol, 95%) as a brown amorphous solid. MS (ES) m/e 324 [M+H]+.

Workup

temperaturemaintained at that temperature for one hour
temperatureto cool to room temperature before it
washThe organic layer was washed with water (3×20 mL) and brine (3×20 mL)
dry with materialThe organic phase was dried over Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-38d74539e7a04bb3926f3a7cf88e8816
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432258B2

Reaction notes

Loading…