* 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.
Reference：
[1] Journal of Agricultural and Food Chemistry, 2005, vol. 53, # 21, p. 8148 - 8155
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Yield
Reaction Conditions
Operation in experiment
72%
With ammonium hydroxide; iodine; potassium iodide In water at 20℃; for 6 h;
To a well stirred solution of KI (1.0 mmol) and I2 (1.0 mmol) in NH4OH (aq) 30percent (5.0 ml) was added p-hydroxybenzaldehyde (1.0 mmol) and the resulting mixture was allowed to react for 6 h at room temperature. The solution was then acidified with HCl (aq) 10percent, and extracted with Et2O (2 x 10 ml). The combined organic phases were dried over Na2SO4 and evaporated to dryness. The desired product was obtained after crystallization from H2O. Yield = 72 percent. Analytical data were identical to those already reported for the same compound.3 Anal. Calcd for C7H5IO2: C, 33.90; H, 2.03; O, 12.90. Found: C, 33.93; H, 2.06, O, 12.94.
70%
With potassium hydrogensulfate; isoquinolinium dichromate; potassium iodide In water at 50 - 60℃;
General procedure: A centimolar (0.01mol) organic substrate (phenols, anilines,or acetanilides), about 0.01 mol of potassium halide (KBr orKI), 0.001 mol hypervalent Cr (VI) reagent (IQCC orIQDC), and solvent (DCE or ACN) were taken in a previouslycleaned round-bottom flask. About 50 mg of KHSO4 isalso added to the reaction flask. The reaction mixture isrefluxed for about 4–5 h at 50–60C. Progress of the reactionwas monitored by TLC technique. After completion, thereaction mixture is treated with 5percent sodium thiosulfate solutionfollowed by the addition of ether. The aqueous layer wasseparated, dried, and evaporated under vacuum, and purifiedwith column chromatography using chloroform:n-hexane(9:1) as eluent to get pure product.General
70%
With tetra-(n-butyl)ammonium iodide; isoquinolinium chlorochromate In water at 25 - 30℃; for 4 h;
General procedure: Phenol (1 mmol, 10 mL) dissolved in 1M PEG-600, isoquinolinium dichromate (IQDC) or isoquinolinium chlorochromate (IQCC) reagent, and tetrabutylammonium halide (TBAX) (1.1 mmol each) were taken in a reaction flask and refluxed with constant stirring at about 25 to 30 C, till the completion of reaction, as as certainedby thin layer chromatography. Then the contents of reaction were diluted with ethyl acetate (10 mL) and separated from aqueous layer. Organic layer was then washed two to three time swith 5 mL water and separated. Finally, the resultant mass is dried over sodium sulphate. The anhydrous ethyl acetate layerwas separated under reduced pressure to give crude product, which was further purified by column chromatography (silicagel, 100-200 mesh) using EtOAc-hexane (3:7). For the separation and recyclization of PEG, aqueous mother liquor (reaction mixture of PEG-600 and water) was treated with ether because PEG is insoluble in ether. The aqueous layer obtained after the removal of ether, was then distilled directly at 100 C to remove water and recover PEG-600. The recovered PEG-600 could be reused for consecutive runs.
50%
With N-iodo-succinimide In acetic acid at 20℃; for 16 h;
INTERMEDIATE 394-Hydroxy-3-iodobenzaldehydeTo a stirred solution of 4-hydroxybenzaldehyde (2.0 g, 16.39 mmol) in AcOH (30 mL) was added N-iodosuccinimide (4.5 g, 19.67 mmol). The reaction mixture was stirred at r.t. for 16 h, then filtered. The filtrate was poured onto water (100 mL) and EtOAc (50 mL) was added. The aqueous fraction was separated, then extracted with EtOAc (3 x 50 mL). The combined organic fractions were washed with water (2 x 20 mL), dried (Na2SO4), filtered and concentrated in vacuo to give the title compound (2.0 g, 50percent) as a white solid that was used without further purification. LCMS (ES-) 247.1 (M-H)", RT 1.44 minutes {Method 9).
49%
for 12 h; Inert atmosphere
4-Hydroxybenzaldehyde 32a (5.0 g, 40.90 mmol)Was dissolved in 30 mL of glacial acetic acid,N-Iodosuccinimide (9.20 g, 40.90 mmol)Of glacial acetic acid solution, then add lmL concentrated sulfuric acid, stirring reaction for 12 hours.The reaction solution was poured into 50 mL of water, extracted with ethyl acetate (50 mL of X3) and the organic phases were combined, washed with saturated sodium chloride solution (50 mL of X3), dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure. Silica gel column chromatography The resulting residue was purified with eluent system A to give the title product, 4-hydroxy-3-iodobenzaldehyde 32b (5.0 g, yellow liquid), yield: 49.0percent.
Reference：
[1] Organic Preparations and Procedures International, 2002, vol. 34, # 6, p. 647 - 651
[2] Journal of the Brazilian Chemical Society, 2010, vol. 21, # 1, p. 3 - 6
[3] Journal of Organic Chemistry, 2002, vol. 67, # 24, p. 8622 - 8624
[4] Synthesis, 2010, # 9, p. 1467 - 1472
[5] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 2, p. 769 - 772
[6] Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 2016, vol. 46, # 6, p. 832 - 837
[7] Asian Journal of Chemistry, 2018, vol. 30, # 8, p. 1892 - 1896
[8] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 12, p. 3147 - 3149
[9] Helvetica Chimica Acta, 1993, vol. 76, # 1, p. 425 - 430
[10] Journal of Organic Chemistry, 1995, vol. 60, # 21, p. 6829 - 6839
[11] Patent: WO2009/1089, 2008, A1, . Location in patent: Page/Page column 36
[12] Patent: CN103030646, 2016, B, . Location in patent: Paragraph 0630; 0632-0635
[13] Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 2011, vol. 41, # 3, p. 258 - 261
[14] Journal of Organic Chemistry, 2013, vol. 78, # 17, p. 8680 - 8688
[15] Journal of the Chemical Society, 1950, p. 2824,2830
[16] Journal of medicinal chemistry, 1996, vol. 39, # 24, p. 4804 - 4809
[17] Journal of Medicinal Chemistry, 1999, vol. 42, # 18, p. 3572 - 3587
[18] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 2, p. 463 - 466
[19] Carbohydrate Research, 2005, vol. 340, # 1, p. 15 - 24
[20] Patent: WO2010/123975, 2010, A1, . Location in patent: Page/Page column 89-90
[21] Patent: US2011/3785, 2011, A1, . Location in patent: Page/Page column 13
[22] Patent: US2013/281398, 2013, A1, . Location in patent: Paragraph 0458; 0459
[23] Patent: WO2018/64135, 2018, A1, . Location in patent: Paragraph 0221-0224
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Reference：
[1] Synthesis, 2010, # 16, p. 2776 - 2786
[2] Angewandte Chemie - International Edition, 2013, vol. 52, # 40, p. 10635 - 10638[3] Angew. Chem., 2013, vol. 125, # 40, p. 10829 - 10832,4
[4] Journal of Organic Chemistry, 2017, vol. 82, # 2, p. 1205 - 1217
5
[ 67-66-3 ]
[ 533-58-4 ]
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[ 23602-64-4 ]
Reference：
[1] Journal of the American Chemical Society, 1950, vol. 72, p. 4324
6
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Reference：
[1] Angewandte Chemie - International Edition, 2013, vol. 52, # 40, p. 10635 - 10638[2] Angew. Chem., 2013, vol. 125, # 40, p. 10829 - 10832,4
7
[ 123-11-5 ]
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Reference：
[1] Journal of Organic Chemistry, 2017, vol. 82, # 2, p. 1205 - 1217
8
[ 123-08-0 ]
[ 1948-40-9 ]
[ 60032-63-5 ]
Reference：
[1] Chemische Berichte, 1895, vol. 28, p. 2410
5-[(3-(S)-amino-2-oxopyrrolidin-1-yl)methyl]-2-hydroxybenzonitrile hydrochloride2-yl1-(3-cyano-4-(2-methoxyethoxymethoxy)benzyl)pyrrolidin-2-one hydrochloride[ No CAS ]
With boron tribromide; In dichloromethane; at 0 - 20℃; for 24h;
Approximately 1 g of 3-iodo-4-methoxybenzaldehyde was added to 100 mL of anhydrous dichloromethane and stirred at 0 C. 0.405 mL of boron tribromide was added dropwise to the solution and was allowed to warm to room temperature over a period of 24 hours. Approximately 40 mL of water was then added to the solution to quench the reaction. The aqueous and organic layers were then separated and the aqueous layer was extracted with two 100 mL washings of ethyl acetate. The ethyl acetate layers were collected and combined with the organic layer from the initial separation. The combined organic layer was washed with 100 mL of water and 100 mL of brine and was then dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. Thin layer chromatography was then applied to the crude product to determine the conditions for optimal separation by silica gel flash column chromatography. A mobile phase composition of 80% hexanes and 20% ethyl acetate provided the best separation of product from starting material. Fractions collected from the column which contained the product compound were combined and concentrated under vacuum. The final yield of purified product was approximately 46%. FIG. 3 and FIG. 4 show the respective proton NMR spectrum and MALDI MS of the synthesized 4-hydroxy-3-iodobenzaldehyde. 1H NMR (400 MHz, CDCl3) delta 9.81 (s, 1H), 8.22 (s, 1H), 7.80 (d, J=6.8 Hz, 1H), 7.12 (d, J=8.3 Hz, 1H), 5.84 (s, 1H). MALDI MS (M+H+) m/z 248.238.
With copper(l) iodide;bis-triphenylphosphine-palladium(II) chloride; In propargyl alcohol; N,N-dimethyl-formamide; at 20℃; for 24h;Inert atmosphere;
Example 22. Preparation of 2-(2-hydroxymethyl-benzofuran-5-yl)-5,7-dimethoxy-3H-quinazolin-4-one[0243] To a solution of 4-hydroxy-benzaldehyde (3.66 g, 30.0 mmol) in 50% (v/v) aqueous ammonium hydroxide (250 mL) was quickly added a solution of potassium iodide (24.9 g, 150 mmol) and iodine (7.62 g, 30.0 mmol) in water (60 mL). The dark colored solution was stirred at room temperature for 1 hour and the color changed to yellow. Stirring was continued at room temperature for 16 hours. The color changed to gray. Then, the reaction mixture was filtered through a celite pad. The filtrate was acidified with concentrated HCI to pH approximately 1 and extracted with ethyl acetate (1 * 300 ml_). The organic phase was washed with water (150 ml_) and brine (150 ml_), dried over anhydrous Na2SO4, and concentrated to give <strong>[60032-63-5]4-hydroxy-3-iodo-benzaldehyde</strong> as an off-white solid (1 :1 mixture of starting material and product). Yield: 5.34 g (crude). [0244] To a degassed solution of <strong>[60032-63-5]4-hydroxy-3-iodo-benzaldehyde</strong> (5.34 g, 15.0 mmol) in anhydrous DMF (100 ml_) were added bis(triphenylphosphine)palladium(ll) dichloride (0.53 g, 0.75 mmol), copper (I) iodide (0.14 g, 0.75 mmol), 1,1,3,3-tetramethyl guanidine (8.64 g, 75.0 mmol), and propargyl alcohol (1.18 g, 21.0 mmol). The reaction mixture was stirred at room temperature for 24 hours under nitrogen and then concentrated to dryness under reduced pressure. The residue was diluted with 2 N aqueous HCI (150 ml_) and extracted with ethyl acetate (1 x 200 ml_). Organic phase was washed with water (2 x 100 ml_), brine (100 ml_), and dried over anhydrous Na2SO4. Solvent was evaporated and crude compound was purified using the Simpliflash system (30% ethyl acetate in hexanes as eluent) to give 2-hydroxymethyl-benzofuran-5-carbaldehyde as a pale yellow solid. Yield: 1.36 g (26% for two steps). [0245] To a solution of 2-hydroxymethyl-benzofuran-5-carbaldehyde (0.450 g, 2.55 mmol) and 2-amino-4,6-dimethoxy-benzamide (0.500 g, 2.55 mmol) in N,N-dimethylacetamide (5 mL) were added sodium hydrogen sulfite (58.5 wt %; 0.510 g, 2.80 mmol) and p-toluenesulfonic acid (50 mg, 0.25 mmol). The reaction mixture was stirred at 1200C for 6 hours under nitrogen and cooled to room temperature. The separated solid was filtered, washed with ether (30 mL), water (30 mL), and ethyl acetate (20 mL), and then dried under vacuum to give the title compound as a yellow solid. Yield: 0.572 g (64%). 1H NMR (400 MHz, DMSO-de): delta 12.07 (br s, 1 H), 8.44 (d, J = 2.0 Hz, 1 H), 8.10 (dd, J = 8.8 and 1.6 Hz, 1 H), 7.67 (d, J = 8.8 Hz, 1 H), 6.89 (s, 1 H), 6.76 (d, J = 2.4 Hz, 1 H), 6.54 (d, J = 2.4 Hz, 1 H), 4.61 (s, 2H), 3.90 (s, 3H), 3.86 (s, 3H). MS (ES+) m/z: 353.20 (M+1).
Na (5.0 mmol) was dissolved in dry MeOH (7 ml) and to the resulting solution methyl trimethylphosphonacetate (3.0 mmol) and a solution of the aldehyde (1.0 mmol) in dry MeOH (1 ml) were added in sequence. The resulting mixture was allowed to react for 24 h at 70 C. The solution was then acidified with HCl (aq) 10%, and extracted with Et2O (3 x 10 ml). The combined organic phases were dried over Na2SO4 and evaporated to dryness yielding the desired product that was used for the next reaction without further purification.
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