2-Bromo-3,5-dimethoxybenzaldehyde synthesis

8synthesis methods

Product Name:2-Bromo-3,5-dimethoxybenzaldehyde
CAS Number:85565-93-1
Molecular formula:C9H9BrO3
Molecular Weight:245.07

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Yield:85565-93-1 98%

Reaction Conditions:

with N-Bromosuccinimide in dichloromethane at 20; for 18 h;

Steps:

2-Bromo-3,5-dimethoxybenzaldehyde (S51)

Small scale: To a solution of 3,5-dimethoxybenzaldehyde (S50, 1.0 equiv, 0.84 g, 5.02 mmol) in DCM (14 mL) at 0 °C was added NBS (1.0 equiv, 0.89 g, 5.02 mmol) portionwise. The reaction was stirred at rt for 18 h. The reaction was then quenched by addition of a saturated solution of NaHCO₃ (20 mL) and poured onto water (20 mL). The organics were extracted with DCM, combined, washed with NaHCO₃, dried over MgSO₄ andconcentrated in vacuo. Pure S51 was obtained as a white solid (1.12 g, 4.55 mmol, 91 %). Gram-scale: Following the same procedure, S51 was obtained as a white solid (14.0 g, 57.1 mmol, 98 %) from3,5-dimethoxybenzaldehyde (S50, 1.0 equiv, 10.0 g, 60.2 mmol) and NBS (1.0 equiv, 10.7 g, 60.2 mmol). Mp: 102-104 °C (lit. 110-112 °C)⁵⁴; A small difference between the experimental and the reported melting point was noted; ¹H NMR (400 MHz, CDCl₃) δ_H 10.40 (s, 1H, CHO), 7.03 (d, J = 2.8 Hz, 1H, ArH), 6.70 (d, J= 2.8 Hz, 1H, ArH), 3.91 (s, 3H, OCH₃), 3.84 (s, 3H, OCH₃). Spectral data in accordance with those reported in the literature.⁵⁴