2-Chloro-1,3-dimethoxybenzene

General procedure: In a 5mL crimp cap vial 0.25mmol of the respective substrate, together with 0.3mmol (1.2equiv) of the N-chloramine or NCS, 0.3mmol (1.2equiv) (NHGeneral 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: Similar to the procedure by An et al. [1], to a solution of the catechol (13), resorcinol (8 or 14), or hydroquinone (crude 16, cf. below, or 18) (1.0 equiv) in acetone (0.1 M), potassium carbonate (5.0 equiv) was added and the mixture was stirred for 10 min. Methyl iodide (2.6 equiv) was added and the reaction mixture was stirred under reflux for 16 h. After cooling to room temperature water was added and the mixture was extracted three times with diethyl ether. The combined organic extracts were dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel to afford the pure compounds 4c (from 8), 10b (from 13), 10h (from 14), 10i (from crude 16), and 10k (from 18). 2-Chloro-1, 3-dimethoxybenzene (4c): Pale yellow solid (76 mg, 0.44 mmol, 88percent). TLC (hexane/ethyl acetate 10:1) Rf 0.38; IR (ATR) 3011 (w), 2966 (w), 2947 (w), 2840 (w), 1594 (m), 1472 (m), 1435 (m), 1299 (m), 1253 (m), 1191 (w), 1174 (w), 1099 (m), 1053 (m), 1025 (m), 849 (w), 764 (m), 709 (m), 654 (m), 597 (m); UV–vis λmax (log ε) 280 (3.08), 274 (3.10), 230 (3.79) nm.To a solution of 1, 3-dimethoxybenzene (13.8 g) in dry ether (50 ml, freshly distilled from sodium benzophenone ketyl) is added dropwise 2.4M n-butyllithium (50 ml) at 5° C. over five minutes. (e)

Molecular Weight:172.61
XLogP3:2.1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:172.0291072
Monoisotopic Mass:172.0291072
Topological Polar Surface Area:18.5
Heavy Atom Count:11
Complexity:107
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes