Water → [4-(2-Nitro-4-trifluoromethyl-phenoxy)-phenyl]-acetic acid methyl ester

HRID 1983209Notes

Reaction equation

F[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[OH:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[CH3:26][O:25][C:23](=[O:24])[CH2:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=2[N+:12]([O-:14])=[O:13])=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 4-fluoro-3-nitrobenzotrifluoride (1a, 1.0 g, 4.78 mmol), methyl 4-hydroxyphenylacetate (1b, 795 mg, 4.78 mmol) and potassium carbonate (661 mg, 4.78 mmol) in 10 mL of DMSO was allowed to stir at 60° C. for 24 h. Upon completion, the mixture was cooled to room temperature and 50 mL of water was added. The resulting mixture was extracted with ethyl acetate (3×30 mL). The combined extracts were washed with water (2×30 mL) and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was chromatographed on a silica gel column using 20% EtOAc/hexane as the eluent to give 1.31 g of [4-(2-nitro-4-trifluoromethyl-phenoxy)-phenyl]-acetic acid methyl ester. 1H NMR (CDCl3): δ 8.22 (d, J=2.00 Hz, 1H), 7.70 (dd, J=8.8, 2.2 Hz, 1H), 7.36 (d, J=8.36 Hz, 2H), 7.08 9s, 1H), 7.07 (d, J=8.48 Hz, 2H).

Workup

temperatureUpon completion, the mixture was cooled to room temperature
extractionThe resulting mixture was extracted with ethyl acetate (3×30 mL)
washThe combined extracts were washed with water (2×30 mL) and brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record: ord-4c71290902734ee3aeeedc5b20249b6c
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07541383B2

Reaction notes

Loading…