2-IODO-1 3-DIMETHOXYBENZENE97

To a solution of 1, 3-dimethoxybenzene (25 g, 180 mmol) in diethyl ether (150 mL) was slowlyadded butyllithium (112.5 mL of 1.6 M solution in hexanes, 180 mmol). The reaction was stirred for30 h and then cooled to -35°C. Iodine (45.7 g, 180 mmol) was added and the reaction was stirredfor 24 h at 20°C and then poured into 10percent chloridric acid (60 mL). The aqueous phase wasseparated and extracted with ethyl acetate (2 × 60 mL) and the combined organic extracts washedwith saturated aqueous sodium thiosulfate (60 mL), brine (60 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The product was purified by crystallization (diethylether) to give 16 (34g, 71percent) as a white solid; mp 105-106 °C (Lit.104 °C) [1] ; 1H NMR (CDCl3): δ 3.80 (s, 6H), 6.43 (d, J 8.4, 2H), 7.17 (t, J 8.4, 1H); 13C NMR (CDCl3): δ 56.6, 76.3, 103.9, 129.8, 159.5; Anal.Calcd for C8H9IO2: C, 36.39; H, 3.44; Found: C, 36.40; H, 3.46.(1) Synthesis of intermediate 2 2, 6-Dimethoxybenzene 1(50 g, 0.36 mol) was dissolved in absolute THF (500 ml). A solution of n-butyl lithium in n-hexane (166 ml, 0.42 mol) was slowly added thereto at 0°C under the nitrogen atmosphere. To the resultant solution, a solution of iodine (96.5 g, 0.38 mol) dissolved in absolute THF (200 ml) was added dropwise at 0°C over 40 minutes. The resultant solution was stirred at room temperature overnight. After completion of stirring, methanol (80 ml) was added dropwise, and the resultant mixture was concentrated under the reduced pressure, and after adding water (200 ml), the mixture was extracted with ethyl acetate (250 ml) 3 times. Organic layers were combined, and said organic layer was washed with Na2, 6dimethoxybenzene (B141, 50 g0.36mol) was dissolved in the drying THF (500 mL). Thenhexane solution (166 mL, 0.42 mol) of nbutyl lithium was gradually added here at 0 degreeC under a nitrogen atmosphere. It was dropped at it at 0 degree C, having covered [ of theiodine (96.5 g0.38mol) in which the drying THF (200 mL) was dissolved ] it over the solutionobtained here for 40 minutes. The obtained solution was stirred at the room temperature allnight. After condensing under decompression of the mixture obtained by dropping methanol(80 mL) after an end and adding water (200 mL), ethyl acetate (3x250 mL) extracted. After itcollected organic layers and Na S O and a salt solution washed the organic layer, it dried usingsodium sulfate.Mineral salt was filtered after drying and it condensed under decompression, and when residuewas washed 4 times and dried with methanol (50 mL), the 2, 6dimethoxyiodobenzene (B142) was obtained as a yellow solid (63 g0.24mol, 66percent yield).General procedure: A solution of 2, 6-dimethoxybenzoic acid (0.1 mmol), iodine reagent, palladium catalyst, solvent (1.0 mL) was added to 10 mLIn the reaction vessel, Access to nitrogen protection, Heating reaction, The product was analyzed by GC-MS. The specific reaction conditions of each control group were shown in Table 1.Silak reaction tube equipped with a magnetic stirrer was charged with 3.1 mg of silver sulfate, 36.3 mg of copper acetate, 36.4 mg of 2, 6-dimethoxybenzoic acid, 149.9 mg of sodium iodide and 1 mL of dimethylsulfoxide.The reaction was heated at 160 ° C for 24 hours in the presence of oxygen.After the reaction was completed, distilled water was added to quench the reaction, Extraction with ethyl acetate 3 times, each time 10mL, The combined organic phases are concentrated, 19.5 mg of 2, 6-dimethoxy-iodobenzene was obtained in a yield of 37percent.

Molecular Weight:264.06
XLogP3:3.2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:263.96473
Monoisotopic Mass:263.96473
Topological Polar Surface Area:18.5
Heavy Atom Count:11
Complexity:107
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes