Structure of 55894-18-3
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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 55894-18-3 |
Formula : | C15H32BrP |
M.W : | 323.29 |
SMILES Code : | CCCC[P+](CCCC)(CC=C)CCCC.[Br-] |
MDL No. : | MFCD01706152 |
InChI Key : | GGJHLMANZFSVPZ-UHFFFAOYSA-M |
Pubchem ID : | 3043640 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319 |
Precautionary Statements: | P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 |
* 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 |
---|---|---|
In dichloromethane; at 0 - 20℃; for 10.5h;Inert atmosphere; | To a mixture of tributylphosphine (20.00 g, 98.85 mmol, 1.00 eq) in DCM (30.00 mL) was added 3-bromoprop- l-ene (13.16 g, 108.74 mmol, 1.10 eq) at 0 C under N2. The mixture was stirred at 0 C for 0.5 h and then warmed to room temperature and stirred for 10 h. The mixture was concentrated to afford crude allyltributylphosphonium bromide (32.00 g, 98.98 mmol) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | In lithium hydroxide monohydrate; at 50℃; for 1h; | Tri-n-butyl(2-propen-1-yl)phosphonium bromide (5.005 g,15.48 mmol) and lithium bis(trifluoromethanesulfonyl)imide(4.759 g, 16.58 mmol) were combined in a round bottom flaskequipped with a magnetic stir bar and dissolved in 50 mL deionizedwater forming a cloudy solution. The mixture was stirred for1 hr at 50 C and then allowed to cool to room temperature. Themixture was transferred to a separatory funnel, and the productwas extracted twice with 10 mL dichloromethane. The organiclayer was washed twice with 10 mL deionized water. Solventwas removed via rotary evaporation. The resulting solid was driedon a vacuum line and stored in a desiccator. Yield: white solid,7.810 g, 97%. Characterization and spectroscopy agree with literatureprecedent [33]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.77% | To a mixture of <strong>[55894-18-3]allyltributylphosphonium bromide</strong> (28.65 g, 88.63 mmol, 1.10 eq) in water (30.00 mL) was added NaOH (12.89 g, 322.28 mmol, 4.00 eq) at 0 C. The mixture was stirred at 0 C for 0.5 h before addition of 2-fluorobenzaldehyde (10.00 g, 80.57 mmol, 1.00 eq). The mixture was warmed to room temperature and stirred for 0.5 h. This mixture was then heated to 70 C-80 C and stirred for 2 h. The reaction mixture was diluted with water (100 mL), extracted with DCM (20 mL * 3), and the combined organic s phase dried over Na2S04, filtered, and concentrated. The crude residue was purified by column chromatography (Si02, DCM: MeOH = 1: 0) to afford (E)-l-(buta-l,3-dien-l-yl)-2- fluorobenzene (10.00 g, 67.49 mmol, 83.77% yield) as a yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85.8% | With bromine; In chloroform; at -5 - 0℃; | General procedure: To a solution of 1.5 g (4 mmol) of phosphonium salt 1 in 15 mL of chloroform cooled to 0 to -5 0.64 g (4 mmol) of bromine was added dropwise at vigorous stirring. The reaction mixture was warmed to room temperature, the solvent removed in a vacuum, the residue was washed with dry benzene, then dry ether, and dried in a vacuum to obtain 2.11 g (97%) of 2,3-dibromo-propyl-triphenylphosphonium bromide 3, mp 165-166. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sodium hexafluorophosphate(V); In lithium hydroxide monohydrate; at 20℃; for 24h; | Tri-n-butyl(2-propen-1-yl)phosphonium bromide (1.500 g,4.64 mmol) was dissolved in 80 mL deionized water in a round bottomflask equipped with a magnetic stir bar. Sodium hexafluorophosphate(1 eq., 0.774 g, 4.61 mmol) was dissolved separatelyin 30 mL deionized water and added to flask, forming a cloudysolution. The mixture was stirred at room temperature for 24hrs. The resulting white precipitate was isolated via filtration andwashed with deionized water. The solid was dried on a vacuumline and stored in a desiccator. Yield: white solid, 1.521 g, 85%.Melting point (visual): 208 C. 1H NMR (400 MHz, CD3OD): dH(ppm) = 5.82 (m, 1H), 5.45 (m, 2H), 3.13 (q, J = 7.7 Hz, 2H), 2.20(m, 6H), 1.58 (m, 12H), 0.99 (t, J = 7.2 Hz, 9H). 13C NMR(101 MHz, CD3OD): dC (ppm) = 125.63 (d, J = 9.7 Hz), 124.42 (d,J = 11.9 Hz), 25.07 (d, J = 47.8 Hz), 24.86 (d, J = 15.6 Hz), 24.20(d, J = 4.51 Hz), 18.93 (d, J = 47.7 Hz), 13.58 (s). 19F NMR(376 MHz, CD3OD): dF (ppm) = -71.84 (d, J = 708.2 Hz). 31P NMR(162 MHz, CD3OD): dP (ppm) = 32.18 (s), 144.17 (sep,708.5 Hz). FTIR-ATR (cm1): 2963, 2937, 2877, 1638, 1467, 1422,1407, 1384, 1348, 1316, 1284, 1233, 1208, 1100, 1086, 1053,993, 969, 931, 917, 876, 825, 753, 741, 719, 593, 569, 556. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With 2,2-dimethoxy-2-phenylacetophenone; In methanol; for 1h;UV-irradiation; | Tri-n-butyl(2-propen-1-yl)phosphonium bromide (1.537 g,4.75 mmol), 1H,1H,2H,2H-perfluorodecanethiol (2 eq., 4.513 g,9.40 mmol), and DMPA (0.05 eq., 0.064 g, 0.25 mmol) were combinedin a 20 mL scintillation vial equipped with a magnetic stirbar and dissolved in 7.5 mL methanol to form a colorless solution.The mixture was irradiated under UV light for 1 hr with constantstirring, producing a white suspension. The suspension was transferredto a round bottom flask and solvent was removed via rotaryevaporation. The crude product was stirred with 60 mL hexanes for1 hr at room temperature, forming a mixture with two liquidphases. The top solvent layer was decanted, leaving a viscous oilthat was stirred with an additional 60 mL hexanes at 50 for 1hr. Solvent was again decanted and the purified oil was dried ona vacuum line, eventually affording a white solid that was subsequentlystored in a desiccator. Yield: white solid, 3.522 g, 92%.Melting point (DSC): 46 C. 1H NMR (400 MHz, CD3OD): dH(ppm) = 2.80 (m, 4H), 2.51 (m, 2H), 2.38 (m, 2H), 2.26 (m, 6H),1.88 (m, 2H), 1.55 (m, 12H), 1.01 (t, J = 7.0 Hz, 9H). 13C NMR(101 MHz, CD3OD): dC (ppm) = 33.36 (d, J = 17.3 Hz), 32.91 (t,J = 21.8 Hz), 24.97 (d, J = 15.6 Hz), 24.44 (d, J = 4.6 Hz), 23.29 (t,J = 4.1 Hz), 22.54 (d, J = 3.6 Hz), 19.22 (d, J = 48.5 Hz), 18.49 (d,J = 48.5 Hz), 13.70 (s). 19F NMR (376 MHz, CD3OD): dF (ppm) =-82.38, 115.21, 122.71, 122.89, 123.74, 124.27, 127.28.31P NMR (162 MHz, CD3OD): dP (ppm) = 34.16. HRMS (ESI/QTOF)m/z: [M - Br]+ calculated for C25H37F17PS: 723.2082, found:723.8196. FTIR-ATR (cm1): 2960, 2934, 2909, 2873, 2807, 1465,1450, 1417, 1367, 1330, 1314, 1237, 1199, 1145, 1135, 1115,1085, 1033, 997, 970, 955, 918, 901, 871, 825, 803, 777, 764,745, 737, 725, 705, 684, 657, 621, 619, 605, 595, 587, 580, 573,559, 537, 533. |