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CAS No. : | 57455-06-8 | MDL No. : | MFCD00004635 |
Formula : | C7H7IO | Boiling Point : | 254.7°C at 760 mmHg |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 234.03 g/mol | Pubchem ID : | - |
Synonyms : |
|
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: |
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Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With thionyl chloride In dichloromethane at 20℃; for 30 h; Reflux | A solution of 3-iodobenzyi alcohol (600 mg, 2.56 mmol) in DCM (3ml) was treated with thionyl chloride (3 ml, 41.3 mmol) and stirred at ambient temperature for 18h, before addition of further thionyl chloride (1 ml, 13.7 mmol) and heating to reflux for 12h. The cooled solution was basified with 50percent NaOH, diluted with water and extracted with DCM, The combined organics were dried over MgS04, filtered and evaporated to afford a clear syrup which crystallises on standing to give 3-iodobenzyl chloride as a white solid (650mg, quant.). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With pyridinium chlorochromate In dichloromethane at 20℃; for 2 h; | 3-Iodobenzaldehyde (12) A suspension of pyridinium chlorochromate (2.45 g, 11.4 mmol) and dry celite (-2. 00 g) in dry dichloromethane (20 ml) was stirred at room temperature for 15 min. 3-Iodobenzyl alcohol (11) (1.02 g, 4.35 mmol) in dry dichloromethane (5 ml) was added. The suspension was shielded from light and stirred at room temperature for 2 h after which it was diluted with ether, and filtered through celite. The cloudy brown filtrate was concentrated to a red- brown gummy paste which was re-dissolved in dichloromethane and passed through a short silica column, eluting with dichloromethane. This gave a clear, colourless solution which was concentrated to give 3-iodobenzaldehyde (12) as a white solid (0.953 g, 95percent). 1H nmr (400 Mz, CDC13) : 67. 29 (t, J 7. 8 Hz, 1H) H5; 7.85 (brd, J 7. 8 Hz, 1H) H6; 7.96 (brd, J7. 8 Hz, 1H) H4; 8.21 (brs, 1H) H2; 9.93 (s, 1H) CHO. |
80% | With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide In dichloromethane; acetonitrile at 20℃; for 3 h; 4 A molecular sieves | A solution of 3-iodobenzyl alcohol (Aldrich, 4.72g, 20 mmol) in dichloromethane (50mL) and acetonitrile (5mL) was treated sequentially with 4 A molecular sieves powder (5g), tetra-n-propyl ammoniumperruthenate (0. 1 g) and N-methyl morpholine-N-oxide (2.34g, 40mmol). After stirring at ambient temperature for 3h, the reaction mixture was diluted with hexane and subjected to flash column chromatography over silica gel (230-400mesh) using 6-10percent ethyl acetate in hexane as the eluent to afford the title compound (3.7g, 80percent). It was used as such for the next step. |
80% | With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide In dichloromethane; acetonitrile at 20℃; for 3 h; Molecular sieve | 3-Iodo-benzaldehyde; A solution of 3-iodobenzyl alcohol (Aldrich, 4.72g, 20 mmol) in dichloromethane (50mL) and acetonitrile (5mL) was treated sequentially with 4 A molecular sieves powder (5g), tetra-n-propyl ammoniumperruthenate (0. lg) and N- methyl morpholine-N-oxide (2.34g, 40mmol). After stirring at ambient temperature for 3h, the reaction mixture was diluted with hexane and subjected to flash column chromatography over silica gel (230-400mesh) using 6-10percent ethyl acetate in hexane as the eluent to afford the title compound (3.7g, 80percent). It was used as such for the next step |
90 %Chromat. | With dihydrogen peroxide In water; acetonitrile for 4 h; Reflux | General procedure: In a 25 mL round-bottomed flask equipped with a reflux condenser, a mixture of 1 g PWM/SiO2(M = Cr, Mn, Fe, Co, Ni, and Cu)catalyst containing 0.03 mmol POM, 3 mL acetonitrile and 1 mmol of alcohol was added. Then 1 mL of H2O2 30percent was added and the mixture was refluxed for 2 h with stirring. The progress of the reaction was monitored by GC equipped with a flame ionization detector and a silica pack column. At the end of reaction, the catalyst was filtered out and 10 mL NaHCO3 10percent was added. The organic phase extracted with chloroform and dried. Flash chromatography on a short column of silica gel with ethyl acetate:n-hexane as eluent gave pure products. |
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