2-Bromo-1,3,5-trimethoxybenzene

General procedure: A mixture of carboxylic acid (1 equiv., 0.5 mmol), CuBr2 or CuCl2 (2 equiv., 1 mmol), Ag2CO3 (1 equiv., 0.5 mmol) and PdCl2 (0.1 equiv.) was heated inTHF (3 mL) under reflux at 110 oC for 24 h. After the reaction finished, the mixture was evaporated under vacuum and purified by columnchromatography to afford the desired product.General procedure: In a 10 mL two-necked flask equipped with a reflux condenser, substrate (0.25mmol) and tetrabutylammonium bromide (161.2 mg, 0.50 mmol) were placed. The flaskwas evacuated and backfilled with Ar. To the mixture, an ultrapure water (0.5 mL), trifluoroacetic acid (57.5 μL, 0.75 mmol), and 30percent H2O2 (77 μL, 0.75 mmol) wereadded. The mixture was stirred at 25 °C under Ar, followed by treatment with 1:1mixture of saturated Na2S2O3 aqueous solution and saturated NaHCO3 aqueous solution, and extraction with ether. The organic layer was dried over Na2SO4, filtered, andevaporated. 1, 3, 5-Trimethoxybenzene or hexamethylbenzene was added as an internalstandard, and 1H NMR analysis was performed to determine a NMR yield. Spectral dataof the products were identical with those of commercially available and authenticsamples.General procedure: 1-Methoxy-3, 5-dimethylbenzene(100mg, 0.73 mmol), N-Bromosuccinimide (NBS, 260 mg, 1.46 mmol) and one ball (5 mmdiameter, stainless steel) were transferred to a milling jar (10 mL, stainlesssteel). The ball-milling operation was performed and the progress of reaction was monitored by TLC/General procedure: 1-Methoxy-3, 5-dimethylbenzene (100mg, 0.73 mmol), N-Bromosuccinimide (NBS, 260 mg, 1.46 mmol) and one ball (5 mmdiameter, stainless steel) were transferred to a milling jar (10 mL, stainlesssteel). The ball-milling operation was performed and the progress of reactionwas monitored by TLC/General procedure: 1, 4-Dioxane (5 mL) was added to a mixture of substrate (1.5 mmol) and NaBr (3.09 g, 30 mmol). Catalyst 4a, 2.5 mol percent (25 mg, 0.0375 mmol) was dissolved in 15 mL of a pH 4.2 phosphate solution (NaHA pyrex test tube containing solid of 1, 3, 5-trimethoxybenzene (1a, 0.3 mmol), carbon tetrabromide (0.075 mmol), AQN-2-CO2H (0.03 mmol) and dry EtOH (5 mL) was irradiated for 20 h at roomtemperature with stirring by a 21W fluorescent lamp under air. The reactionmixture was concentrated in vacuo, quenched with aq Na2S2O3 and extractedwith EtOAc. The organic layer was dried over MgSO4 and concentrated invacuo. Purification of the residue by flash chromatography on silica gel(hexane/ethyl acetate = 6:1) provided 2-bromo-1, 3, 5-trimethoxybenzene (2a)(66.8 mg, 90percent, ) as a white solid.2', 4', 6'-Trimethoxy-biphenyl-3-carbonyl chloride (51)Step 1: KM03 Dissolve 1, 3, 5-trimethoxybenzene (10.0 g, 59.46 mmol) in anhydrous dichloromethane (10O mL), cool the reaction mixture to -78°C, add dropwise bromine (3.OmL, 59.44 mmol) stir the mixture for Ih between -70To an oven-dried flask fitted with a septum was sequentially added 1, 3, 5-trimethoxybenzene (1.68 g, 10 mmol, 1.0 equiv.), N-Bromosuccinimide (1.78 g, 10 mmol, 1.0 equiv.) and 10 mL anhydrous acetonitrile. The resulting mixture was heated to 800° C. for 5 h under vigorous stirring. At this time, the mixture was cooled to room temperature and filtered. The solvent was removed under vacuum to get a crude product which was purified through silica column with 8 v percent of ethyl acetate in hexane to get a white solid (1.48 g, 60percent). Step 1: General procedure: A mixture of substrate (1 mmol), CuBr

Molecular Weight:247.09
XLogP3:2.5
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:245.98916
Monoisotopic Mass:245.98916
Topological Polar Surface Area:27.7
Heavy Atom Count:13
Complexity:140
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes