Water → HCID 71513519, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 5-methoxy-2-methyl-4-nitrobenzoate (1.11 g, 5 mmol) and NBS (1.07 g, 6 mmol) in MeCN (20 mL) was degassed and then AIBN (18 mg, 0.11 mmol) was added. The mixture was heated to 70° C. for 18 h. DCM (50 mL) and water (50 mL) were added and the organic phase was passed through a hydrophobic frit. The solvent was removed in vacuo and purification of the residue via silica gel column chromatography (0-100% EtOAc in iso-hexane) in order to remove baseline impurities gave methyl 2-(bromomethyl)-5-methoxy-4-nitrobenzoate (477 mg, 31%) as an off-white solid. LCMS (10 cm_ESCI_Bicarb_MeCN): [M−Br]−=224 at 3.92 min. 1H NMR (400 MHz, CDCl3): δ 7.92 (s, 1H), 7.66 (s, 1H), 4.88 (s, 2H), 4.02 (s, 3H), 4.00 (s, 3H).

Provenance & Evidence