1-Bromo-4-(diethoxymethyl)benzene → HCID 57592497, compound

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Reaction Steps

Magnesium turnings (1.4 g) in tetrahydrofuran (10 mL) were stirred under an atmosphere of argon and treated with a solution of 4-bromobenzaldehyde diethyl acetal (15.5 g) in tetrahydrofuran (60 mL) The mixture was stirred for 4 hours then the sulfonyl fluoride D4 (5.46 g) was added and the mixture was stirred for 60 hours. The mixture was poured into a solution of potassium sodium tartrate in water and extracted with ethyl acetate. The residue was purified by column chromatography 0-10% methanol (containing 0.5% aqueous ammonia)-dichloromethane. The product was treated with hydrochloric acid (10 mL) in tetrahydrofuran (100 mL) for 18 hours. The solution was basified and extracted with dichloromethane, and solvent evaporation gave the title compound D11 as a white solid. 1H NMR: δ CDCl3 2.38 (3H, s), 2.6 (4H, m), 2.9 (4H, m), 3.73 (3H, s) 6.65 (1H, s), 7.86 (1H, s), 8.02 (2H, d) 8.12 (2H, d), 10.12 (1H, s).

Provenance & Evidence