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CAS No. : | 63604-94-4 | MDL No. : | MFCD03428523 |
Formula : | C7H7BrO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KHGMUWBYGFWGCZ-UHFFFAOYSA-N |
M.W : | 203.03 | Pubchem ID : | 13493839 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
45% | With palladium diacetate; diisopropylamine; In water; at 100℃; for 1h;Inert atmosphere; Sealed tube; | General procedure: Into a 20 ml_ vial charged with a PTFE-coated magnetic stir bar were added 1 .0 equivalent of arylbromide, 1 .5 equivalent of arylboronic acid and 0.05 equivalent of palladium (II) acetate. The vial was sealed with septa and placed under vacuum and then it was filled with nitrogen. To this vial was added 0.5 M degassed water and 2.0 equivalent of degassed disopropylamine. The reaction mixture was stirred for an hour at 100 C. The mixture was extracted with Ethyl acetate and passed through a pad of celite. The residue was then dried over anhydrous sodium sulfate and removed under reduced pressure. Purification by flash column chromatography (100:0^80:20 hexanes: EtOAc) on Si02 afforded 2a-c as a solid. (0285) 4-methoxy-4"-(pentyloxy)-[1 , 1 ':4', 1 "-terphenyl]-2-ol (2a): (0286) (0287) General procedure II was followed by using 0.50 g of 2-bromo-5methoxyphenol (2.46 mmol), 1 .05 g of (4'-(pentyloxy)-[1 ,1 '-biphenyl]-4-yl)boronic acid (3.69 mmol), 28 mg of palladium (II) acetate (0.12 mmol), 4.9 ml_ water and 0.69 ml_ disopropylamine (4.92 mmol). Purification by flash column chromatography (1 00:0^80:20 hexanes: EtOAc) on Si02 afforded 2a (0.398 g, 45%) as a beige solid, mp = 168-169 C. 1 H NMR (500 (0288) MHz, CDCI3): delta 7.67 (d, J = 8.6 Hz, 2H), 7.57 (d, J = 8.6 Hz, 2H), 7.49 (d, J = 8.6 Hz, (0289) 2H), 7.21 (d, J = 8.4 Hz, 1 H), 7.00 (d, J = 8.6 Hz, 2H), 6.63-6.58 (m, 2H), 5.30 (s, 1 H), (0290) 4.02 (t, J = 6.6 Hz, 2H), 3.85 (s, 3H), 1 .83 (pen, J = 6.8 Hz, 2H), 1 .49-1 .38 (m, 4H), (0291) 0.96 (t, J = 7.2 Hz, 3H); 13C NMR (125 MHz, CDCI3): delta 163.2 (C), 161 .6 (C), 1 56.1 (C), 142.7 (C), 137.8 (C), 135.4 (C), 133.4 (CH), 132.0 (2CH), 130.7 (2CH), 130.2 (2CH), 123.2 (C), 1 17.5 (2CH), 109.7 (CH), 104.0 (CH), 70.7 (OCH2), 58.1 (OCH3), 31 .7 (CH2), 30.9 (CH2), 25.2 (2CH2), 16.7 (CH3); ATR-FTIR (neat): 3392, 2932, 2859, 1 615, 1495, 1288, 1 127 cm"1 ; HRMS (ESI) m/z calculated for C24H2603[M]+: 363.1955, found: 363.1 956. |
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