Benzyl Bromide → 1-(2,4-Bis-benzyloxy-3-iodo-phenyl)-2-methyl-propan-1-one

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Reaction Steps

Combine 1-(2,4-dihydroxy-3-iodo-phenyl)-2-methyl-propan-1-one (1357 g, 4.43 mol), benzyl bromide (1345 mL, 11.28 mol), and cesium carbonate (2460 g, 7.55 mol) in dimethylformamide (12 L) in a 22-L Morton flask and stir at room temperature overnight. Filter the salts and concentrate the filtrate (8 L of dimethylformamide is evaporated off). Combine residue with the salts, dilute with water (10 L) and extract with 2:1 ethyl acetate/toluene (2×6 L). Wash extracts with water (3×4 L), brine, dry with magnesium sulfate, filter, and evaporate. Stir the resulting solid in 9 L of 10% ethyl acetate in hexane for 1 hr, filter, wash solid with hexanes and air dry to provide the title compound (1710 g, 79% yield) as an off-white solid. HPLC Rt=6.60 min; 1H NMR (DMSO-d6) δ 7.61 (d, J=8.0 Hz, 1H), 7.4 (m, 10H), 6.99 (d, J=8.0 Hz, 1H), 5.27 (s, 2H), 4.84 (s, 2H), 3.43 (hept, J=8.0 Hz, 1H), 0.99 (d, J=8.0 Hz, 6H).

Provenance & Evidence