Water → HCID 67330864, compound

HRID 1942480Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

Methyl 4-hydroxy-5-nitro-2-(trifluoromethyl)benzoate (3.0 g) was dissolved in N,N-dimethyl-formamide (50 ml), and thereto were added benzyl bromide (2.3 g) and potassium carbonate (2.3 g), and the mixture was stirred at 80° C. for 6 hours. The reaction mixture was cooled, and water was added thereto. The mixture was extracted with ethyl acetate, and the organic layer was washed twice with water, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (the developing solvent: hexane/ethyl acetate=8:1→5:1→3:1) to give methyl 4-(benzyloxy)-5-nitro-2-(trifluoromethyl)benzoate (2.1 g), which was treated in a similar manner to Reference Example 5 to give the title compound (1.9 g).

Workup

temperatureThe reaction mixture was cooled
extractionThe mixture was extracted with ethyl acetate
washthe organic layer was washed twice with water
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (the developing solvent

Sources & evidence

ORD record: ord-c3f4c4e6aa054e919a99adff032f64fc
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389511B2

Reaction notes

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