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CAS No. : | 74860-13-2 | MDL No. : | MFCD00126843 |
Formula : | C8H8BrNO | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | ZBARBHKSSXDLMK-UHFFFAOYSA-N |
M.W : | 214.06 | Pubchem ID : | 256951 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
14% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; ethanol; water; for 12h;Heating / reflux; | A suspension of Pd (PPH3) 4 catalyst was generated in situ by stirring a mixture of palladium acetate (20.0 mg, 0.09 mmol) and triphenylphosphine (95 mg, 0.36 mmol) in DME (2 mL) under a N2 atmosphere (3 x vacuum and 3 x nitrogen flush). After stirring for 30 minutes, the suspension was introduced via a syringe into a nitrogen-flushed mixture of 5-iso-butyl-2- (N-TERT-BUTYLAMINOSULFONYL) THIOPHENE-3-BORONIC acid (0.57 g, 1.8 mmol; see Example L (c) above), 2- (4-BROMOPHENYL) acetamide (0.39 g, 1.8 mmol; prepared by reaction of 2- (4-BROMOPHENYL) acetonitrile with excess hydrogen peroxide in the presence of potassium carbonate and DMSO at room temperature) and potassium carbonate (0. 96 g, 7.2 mmol) in a solvent mixture of DME, ethanol, and water (7 + 2 + 3 mL). After stirring for 12 h at reflux under a N2 atmosphere, the reaction mixture was diluted with 1M NAOH solution (50 mL) followed by ethyl acetate (150 mL). The organic layer was washed with water and brine, dried over ANHYDROUS MGS04, concentrated in vacuo, and the residue subjected to circular chromatography (75% acetone in petroleum ether). The isolated product (which contained triphenylphosphinoxide) was again purified by preparative LCMS (40-80% aqueous acetonitrile, 0.05% HCOOH, 35 min. duration) to afford the pure sub-title product as colourless solid (100 mg, 0.245 mmol, yield: 14%). IH NMR (270 MHz, CDC13) : 6 0.97 (d, 6H), 1.00 (s, 9H), 1.91 (M, 1H), 2.68 (d, 2H, J= 6.9 Hz), 3.61 (s, 2H), 4.72 (br. s, 1H), 5.70 (br. D, 2H), 6.74 (s, 1H), 7. 35 (d, 2H, J= 7.9 Hz), 7. 58 (d, 2H, J = 8. 3 Hz) 3C NMR (67.5 MHz, CDC13) : 5 22.1, 29.5, 30.5, 39.2, 42.9, 54.5, 128.1, 129.0, 129.5, 133.0, 135. 1, 136.4, 142.8, 148.5, 173.1 IR (neat, CM~') : V3296, 2960,1670, 1311,1142 ESIMS: mlz at 409 (M++1) Anal. Calcd FOR C2OH28N203SZ : C, 58.79 ; H, 6.91 ; N, 6.86 ; Found: C, 58.8 ; H, 7.0 ; N, 6.6 |
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