2-Chloro-4-methoxy-1-methylbenzene

Colorless liquid

Heat a solution of 3-chloro-4-methylphenol (15 g, 0.11 mol), iodomethane (9.8 mL, 0.16 mol), and potassium carbonate (22 g, 0.16 mol) in DMF (200 mL) to 50° C. and stir for 2 hr. To The residue from the previous step was dissolved in 100 mL dioxane, was treated with bis(pinacolato)diboron (11.47 g, 45.2 mmol), potassium phosphate (28.8 g, 135 mmol), XPhos (0.215 g, 0.452 mmol) and (Xphos) palladium(II) phenethylamine chloride (0.334 g, 0.452 mmol) and was heated to 100 C. After stirring overnight, the reaction mixture was concentrated. Silica gel column chromatography (0-20% EtOAc/heptane) gave 2-(5-methoxy-2-methylphenyl)-4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolane (7.80 g, 31.4 mmol, 69.6% yield over two steps). m/z (ESI) 249.3 (M+H)+.A solution of PdCl2(dppf)-DCM adduct (0.922 g, 1.129 mmol), methylboronic acid (2.70 g, 45.2 mmol), 4-bromo-3-chloroanisole (6.39 ml, 45.2 mmol), and potassium phosphate (28.8 g, 135 mmol) in 150 mL dioxane and 50 mL water was heated to 110 C. for 2 hours. The reaction mixture was then diluted with heptane, the organics dried over MgSO4 and concentrated to afford Heat a solution of 2-chloro-4-methoxy-1-methyl-benzene (2.0 g, 13 mmol), N-bromosuccinimide (2.7 g, 15 mmol), and benzoyl peroxide (50 mg) in CCl4 (50 mL) to reflux and stir for 3 hr. Cool the reaction to room temperature and quench with water. Extract the aqueous with CH2Cl2, dry over MgSO4, and filter. Remove the solvent to afford 3.0 g (98%) of the desired product.Example (XX-3) 2-Chloro-4-methoxybenzyl bromide 186 g of Intermediate 49a: 1-Bromomethyl-2-chloro-4-methoxy-benzene BR A suspension of

Molecular Weight:156.61
XLogP3:3.6
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:156.0341926
Monoisotopic Mass:156.0341926
Topological Polar Surface Area:9.2
Heavy Atom Count:10
Complexity:105
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes