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CAS No. : | 1073-67-2 | MDL No. : | MFCD00000632 |
Formula : | C8H7Cl | Boiling Point : | - |
Linear Structure Formula : | (C6H4Cl)CHCH2 | InChI Key : | KTZVZZJJVJQZHV-UHFFFAOYSA-N |
M.W : | 138.59 | Pubchem ID : | 14085 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P501-P261-P270-P210-P271-P264-P280-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330-P302+P352+P312-P304+P340+P312-P403+P235 | UN#: | N/A |
Hazard Statements: | H302+H312+H332-H315-H319-H227 | 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 |
---|---|---|
83% | General procedure: In a pressure tube (glass bomb) a suspension of Pd(OAc)2 (12 mg, 0.05 mmol, 2.5 mol % per Br atom) and dicyclohexyl-(2′,6′-dimethoxybiphenyl-2-yl) phosphine (SPhos) (41 mg, 10 mol %) in DMF (5 mL) was flushed with Ar and stirred at 20 C to give a yellowish or brownish transparent solution. To the stirred solution were added the <strong>[6287-82-7]2,3-dibromobenzothiophene</strong> (15a, 292 mg, 1.0 mmol), Et3N (1.1 mL, 8.0 mmol), and the acrylate (1.25 equiv per Br). The reaction mixture was stirred at 100-130 C for 12-48 h. The solution was cooled to 20 C, poured into H2O and CH2Cl2 (25 mL each), and the organic and the aqueous layer were separated. The latter was extracted with CH2Cl2 (3×25 mL). The combined organic layers were washed with H2O (3×20 mL), dried (Na2SO4), concentrated in vacuo, and passed through a column (silica gel). To a xylene solution (3 mL) of the crude product was added Pd/C (30 mg, 10 mol %). The solution was stirred under reflux for 48 h under argon atmosphere. The reaction mixture was filtered, and the filtrate was concentrated in vacuo. The residue was purified by chromatography (flash silica gel, heptanes-EtOAc) to yield the product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | Example XIIA 5 mL reactor, equipped with a magnetic stirrer, a reflux condenser with an attachment enabling the reaction system to be connected to a vacuum-and-gas line was filled under inert gas with 0.01 g (1.58 10'5 mol) <strong>[69655-76-1]octavinylsilsesquioxane</strong>, followed, in the following order, with 3 mL methylene chloride and 0.015 mL (1.26*10"4 mol) 4- chlorostyrene. The reaction mixture was warmed to 45°C while stirring continuously. Then 0.0009 g (1.26x 10"6 mol) [chlorohydridocarbonylbis(tricyclohexyl- phosphine)ruthenium(II)] was added to the mixture and 5 minutes later 0.0006 g (6.32x 10"6 mol) copper(I) chloride was introduced. The reaction mixture was heated for24 hours at a temperature of 45°C. Then the solvent was subjected to vacuum evaporation and the residue was dissolved in a mixture of hexane and methylene chloride at a ratio by volume of hexane : CH2C12 = 10: 1 and transferred to a silica- packed chromatographic column to purify the product. This produced octakis[2-(4- chlorophenyl)ethenyl]octasilsesquioxane in the form of white powder with a yield of 94percent. Melting range: 300-302°C.lH NMR (C6D6, ppm): delta = 6.44 (d, 8H, J = 19.0 Hz, =CHSi), 6.97 (s, 32H, C6H4-C1),7.53 (d, 8H, J = 19.0 Hz, =CH-Ar)13C NMR (C6D6, ppm): delta = 117.9 (=CHSi), 128.5 (o-C of CeiijCl), 129.2 (m-C of C6H4C1), 135.5 (ipso-C at CI of Q^Cl), 135.7 (ipso-C of C6H4C1), 149.1(=CHAr)29Si NMR (C6D6, ppm): delta = -78.06APPI-MS: m/z ([M+H]+, percent intensity): 1512 (23), 1513 (26), 1514 (57), 1515 (79), 1516 (92), 1517 (95), 1518 (100), 1520 (80), 1521 (65), 1522 (46), 1523 (32), 1524 (20), 1525 (13) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89.5% | With tetrabutylammomium bromide; potassium acetate; palladium diacetate; In N,N-dimethyl-formamide; at 80℃; for 5h;Inert atmosphere; Sealed tube; | General procedure: To a solution of tetrabutylammonium bromide (1.100 g, 3.33mmol), potassium acetate (0.586 g, 3.57 mmol), and palladium acetate (0.025 g, 0.11mmol) in DMF (20 mL) were added substituted iodobenzene (2.21mmol) and substituted styrene (2.44 mmol). The reaction mixture was recharged with argon and stirred at 80C for 5 h in a sealed tube. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous NaCl and concentrated in vacuo. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 10:3) to afford pure product.(E)-4-(4-Chlorostyryl)-1,2-dimethoxybenzene(1).4-Chlorostyrene reacted with 3,4-dimethoxy-iodobenzene following the general procedure (Scheme S1) to give the desired product1(Yield 89.5%Purity 96.6%, CAS: 52792-14-0) as a white amorphous solid.HRMS (ESI) (M+Na)+m/z297.06579, calcd for C16H15ClNaO2297.06528.1H NMR (CDCl3, 500 MHz) δ: 7.35 (d,J= 8.5 Hz, 2H), 7.26 (d,J= 8.5 Hz, 2H), 6.92-7.00 (m, 3H), 6.86 (d,J= 16.0 Hz, 1H), 6.80 (d,J= 8.0 Hz, 1H), 3.90 (s, 3H), 3.85 (s, 3H).13C NMR (CDCl3, 125 MHz) δ: 149.0, 135.9, 132.6, 129.9, 129.0, 128.7, 127.2, 125.2, 119.9, 111.2, 108.8, 55.7. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate; In 1-methyl-pyrrolidin-2-one; at 120℃; for 6h;Inert atmosphere; | General procedure: Amixture of styrene (6a) (2 mmol, 208 mg), alpha-trifluoromethylacrylic acid (2) (0.5mmol, 70 mg), [Cp*RhCl2]2 (0.005 mmol, 3 mg), AgOAc (1 mmol, 167 mg) and1-methylnaphthalene (ca. 40 mg) as internal standard was stirred in NMP (2.5ml) under argon at 120 C for 6h. Then the reaction mixture was diluted byethyl acetate (30 ml). The organic layer was washed by 1 N HCl (30 ml), water30 (ml), and brine (30 ml) and dried over Na2SO4. After evaporation of thesolvents under vacuum, product 7a (101 mg, 93%) was isolated by columnchromatography on silica gel using hexane/EtOAc/AcOH=90/9/1 (v/v/v) as eluent. |
[ 1309676-40-1 ]
1,3-Dichloro-5-(4-chlorostyryl)benzene
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