2,4-Dibromobenzyl Alcohol

54335-33-0

666747-06-4

The general procedure for the synthesis of 2,4-dibromobenzyl alcohol from methyl 2,4-dibromobenzoate was as follows: lithium aluminum hydride (1.14 g, 30 mmol) was slowly added dropwise to a tetrahydrofuran (120 mL) solution of methyl 2,4-dibromobenzoate (5.90 g, 20 mmol) at 0 °C. After the dropwise addition was completed, the ice-salt bath was removed. The reaction mixture was stirred at room temperature for 1 h. The completion of the reaction process was confirmed by liquid chromatography-mass spectrometry (LCMS) and thin layer chromatography (TLC) monitoring. Subsequently, the mixture was cooled again to 0 °C and the reaction was quenched sequentially with water (1.14 mL) and 10% sodium hydroxide solution (11.4 mL). After quenching, stirring was continued for 15 min at room temperature and then the reaction mixture was filtered. The filter cake was washed with tetrahydrofuran (60 mL x 2) and ethyl acetate (60 mL x 2), respectively. The combined filtrates were dried with anhydrous sodium sulfate, filtered and concentrated, and finally purified by column chromatography (elution system: petroleum ether/ethyl acetate = 10:1 to 4:1) to afford the colorless oily product 2,4-dibromobenzyl alcohol (2.3 g, 43% yield). The structure of the product was confirmed by liquid chromatography-mass spectrometry (LC-MS), showing the molecular ion peaks as follows: MS (ESI): m/z 246.9/248.9/250.9 [M-OH]+.