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CAS No. : | 1354819-26-3 | MDL No. : | MFCD18397559 |
Formula : | C7H6BF3O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 221.93 g/mol | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501 | UN#: | |
Hazard Statements: | H302-H312-H332 | Packing Group: | |
GHS Pictogram: |
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* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a solution of 2-hydroxy-5-(thfluoromethoxy)phenylboronic acid (Preparation 23, 20.5 g, 92.4 mmol) and 4-bromo-3-nitro-1 -(tetrahydro-2H-pyran-2-yl)-1 H-pyrazole or 4- bromo-5-nitro-1 -(tetrahydro-2H-pyran-2-yl)-1 H-pyrazole (Preparation 22, 22.7 g, 82.2 mmol) in 1 ,2-dimethoxyethane (300 ml_) and 2 M potassium carbonate in water (1 17 ml_, 212 mmol) was added tetrakis(triphenylphosphine)palladium(0) (5.0 g, 4.3 mmol). The solution was sparged with argon (x 3) and heated at 80 C for 8 hours. The reaction mixture was cooled to ambient temperature and the layers separated. The aqueous phase was washed with ethyl acetate (x 2). The combined organic phase was dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (0 to 30% ethyl acetate in hexanes gradient elution) and concentrated in vacuo. Excess hexanes was added to the residue and the resulting solid was collected by filtration and dried in vacuo to afford the title compound as off white crystals (19.5 g).1H NMR (300 MHz, d6-DMSO): delta 1 .46-1 .78 (m, 3H), 1 .87-2.20 (m, 3H), 3.69 (m, 1 H), 3.97 (d, 1 H), 5.56 (d, 1 H), 6.93 (d, 1 H), 7.22 (d, 1 H), 7.31 (s, 1 H), 8.33 (s, 1 H), 10.19 (br s, 1 H).LCMS Rt = 1 .77 min MS m/z 372 [M-H]- |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A suspension of 2-methoxy-5-(trifluoromethoxy)phenylboronic acid (23.0 g, 97.5 mmol) in dichloromethane (140 ml_) was cooled to 0 C and boron tribromide (9.4 ml_,10 mmol) was added drop-wise over 30 min. After stirring for 3 hours, additional boron tribromide (2 ml_) was added. The reaction mixture was poured into ice water and stirred for 20 min. The dichloromethane was removed in vacuo and the white solid collected by filtration and washed with water before drying in vacuo to afford the title compound(20.8 g). HNMR (d4-Methanol): δ 6.78 (d, 1 H), 7.1 1 (d, 1 H), 7.40 (br s, 1 H).LCMS Rt = 1 .67 min MS m/z 221 [M-H]- |