Hydrochloric Acid → 3-Bromo-2-hydroxybenzaldehyde

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Reaction Steps

To a 500 mL 3-neck round flask, paraformaldehyde (5.96 g, 199 mmol), and 12.60 g of anhydrous MgCl2 (12.60 g, 132 mmol) was added in acetonitrile (300 mL). Then 13.40 g of triethylamine was introduced slowly at room temperature. The mixture was stirred at room temperature for 20 min. 2-bromophenol (11.45 g, 66.2 mmol) was added to the above mixture. Then the reaction mixture was refluxed overnight. Then the mixture was cooled to room temperature, HCl (3N, 150 mL) were added to dilute the mixture. The resulted mixture was filtered through celite, and washed with tertbutyl methyl ether (200 mL). The organic solution was washed with 1N HCl (100 mL×2). The combined acid phase was extracted with EtOAc (100 mL×2). The combined organic layers were washed with brine (100 mL×2), water (100 mL×2), dried over sodium sulphate and concentrated to give 3-bromo-2-hydroxybenzaldehyde (D98) (2.1 g) as yellow oil, which was directly used in next step. MS (ES): C7H5BrO2 requires 199.9. found 201.0 (M+H+).

Provenance & Evidence