2973-58-2

Off-White Solid

Taspine intermediate.

2-Bromo-3-hydroxy-4-methoxybenzaldehyde, also known as 2-bromo-isovanillin, can be synthesized by the bromination of 3-hydroxy-4-methoxybenzaldehyde.

General procedure for the synthesis of 2-bromo-3-hydroxy-4-methoxybenzaldehyde from isovanillin: 3-hydroxy-4-methoxybenzaldehyde (10.0 g, 65.7 mmol) was dissolved in dichloromethane (150 mL), followed by addition of N-bromosuccinimide (NBS, 11.7 g, 65.7 mmol) at room temperature. The reaction mixture was stirred for 30 min at room temperature. Upon completion of the reaction, the target product 2-bromo-3-hydroxy-4-methoxybenzaldehyde (14.1 g, 93% yield) was obtained by conventional post-treatment.

[1] Synthesis (Germany), 2018, vol. 50, # 5, p. 1053 - 1089
[2] Organic and Biomolecular Chemistry, 2018, vol. 16, # 42, p. 7851 - 7860
[3] Organic and Biomolecular Chemistry, 2007, vol. 5, # 9, p. 1466 - 1471
[4] Angewandte Chemie - International Edition, 2011, vol. 50, # 17, p. 3892 - 3894
[5] Synlett, 2000, # 8, p. 1163 - 1165