1-Bromo-2,4-dimethoxybenzene

clearslightlyyellowliqui

General procedure: A 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.General procedure: To a solution of 4-bromoanisole (200.8 mg, 1.09 mmol, 1.0 equiv) in acetonitrile (2 mL) was added N-chlorosuccinimide(NCS) (158.3 mg, 1.19 mmol, 1.1 equiv) at rt to give a slightly cloudy mixture. Chlorotrimethylsilane (TMSCl) (14 μL, 0.11 mmol, 0.1 equiv) was then added drop-wise to the reaction mixture. Within a few minutes, the reaction mixture became clear pale yellow solution. The mixture continued to stir at rt for 1 h and was diluted with hexane. The biphasic mixture was concentrated on a rotary evaporator to a crude white solid-oil mixture. This mixture was taken up in hexane and filtered through a short plug of SiO2 and eluted with 5-10percent EtOAc-hexane solution. The clear filtrate was concentrated to obtain a mixture of 4-bromo-2-chloro-1-methoxybenzene (2a-Cl) and 2, 4-dichloro-1-methoxybenzene (2a-diCl) 237.0 mg (88percent of 2a-Cl and 11percent of 2a-diCl, based on NMR ratio 2a-Cl: 2a-diCl = 7.1: 1.0; as a pale yellow solid).General procedure: 1 mL [Bmim]NO3, 0.5 mmolsubstrate and 0.25 mmol Br2 were added to a dried 45 mL tube equipped witha magnetic stirring (note: the air in the tube was not removed). Then thereaction tube was sealed to perform the reaction at 80 C for 24 h. Once thereaction time was reached, the mixture was cooled to room temperature and3 mL water was added. Then the desired product was extracted with CH2Cl2(3 10 mL). GC analysis of the mixture provided the GC yield of the product.The product in another parallel experiment was purified by columnchromatography, and identified by 1H NMR and 13C NMR.General procedure: A mixture of substrate (1 mmol), CuBrA reaction flask was loaded with 33 m-(MeO)1-bromo-2, 4-dimethoxybenzene 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: A 0.66 M PrA reaction flask was loaded with 33 m-(MeO)

Molecular Weight:217.06
XLogP3:2.8
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:215.97859
Monoisotopic Mass:215.97859
Topological Polar Surface Area:18.5
Heavy Atom Count:11
Complexity:119
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes