Methyl 4-(bromomethyl)-3-methoxybenzoate

STEP 1 : A mixture of methyl 4-methyl-3-(methyloxy)benzoate (1.00 g, 5.55 mmol), N-bromosuccinimide (1.09 g, 6.10 mmol) and a catalytic amount of 2, 2'- azobis(isobutyronitrile) (AIBN) was refluxed in carbon tetrachloride (40 ml) for 16h.The reaction mixture was filtered and the solution was washed with brine (25 ml), General procedure: The reaction mixture was treated in a controlled microwavesynthesizer (Biotage Initiator+SP Wave model, 0–200 W at2.45 GHz, capped at 60 W during steady state) for severalminutes (the reaction attained 120 °C at 1 bar pressure). Thefinal products were isolated by column chromatographyusing an EtOAc–hexane gradientReference Example 49; Methyl 4-(bromomethyl)-3-methoxybenzoate; A mixture of methyl 3-methoxy-4-methylbenzoate (10.0 g, 55.5 mmol), N-bromosuccinimide (10.7 g, 60.9 mmol), 2, 2'-azobis(isobutyronitrile)(1.6 mg) and ethyl acetate (200 ml) was heated under reflux overnight. The solvent was evaporated under reduced pressure, and hexane was added to the residue. The precipitate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with hexane-ethyl acetate (9: 1-7:3, v/v) to give the title compound (12.8 g, 92percent) as a colorless oil. Part F. A. (4-Bromomethyl)-3-methoxybenzoic acid methyl ester: N-bromosuccinimide (7.2 g, 40 mmol) and benzoyl peroxide (40 mg, 0.16 mmol) were added to a stirred solution of 3-methoxy-4-methylbenzoic acid methyl ester (7.2 g, 40 mmol) in chloroform (300 mL). The mixture was then heated at reflux for about 18 hours. The solvent was evaporated and the residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=30/1, 5/1, v/v, elution) to afford the title product (8.25 g, 80percent). To a solution of methyl 3-methoxy-4-methylbenzoate (10 g, 55.6 mmol) and NBS (1 1.8 g, 66.7 mmol) in CCIl. j. D.

Zaffast Intermediate

Molecular Weight:259.10
XLogP3:2.3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:257.98916
Monoisotopic Mass:257.98916
Topological Polar Surface Area:35.5
Heavy Atom Count:14
Complexity:196
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes