ChemicalBook CAS DataBase List 3-Bromo-2-methylbenzaldehyde

3-Bromo-2-methylbenzaldehyde synthesis

4synthesis methods

Product Name:3-Bromo-2-methylbenzaldehyde
CAS Number:83647-40-9
Molecular formula:C8H7BrO
Molecular Weight:199.04

(3-Bromo-2-methylphenyl)methanol (24 g, 119 mmol) was dissolved in dichloromethane (240 mL) and manganese (IV) oxide (103 g, 1.2 mol). After stirring overnight, TLC showed no starting material. The reaction mixture was evaporated with silica gel and loaded on a small silica gel column. After evaporation, the product was eluted with hexane:ethyl acetate (10:1) to give pure aldehyde 3-bromo-2-methylbenzaldehyde (18.6 g).

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Yield:83647-40-9 96%

Reaction Conditions:

with citric acid in tetrahydrofuran;ethyl acetate

Steps:

6.b b
b 3-Bromo-2-methyl-benzaldehyde Lithium aluminum hydride (201 mg, 5.31 mmol) was added in one portion to a -78° C. solution of 3-bromo-N-methoxy-2,N-dimethyl-benzamide ((Example 6: step b) 1.1 g, 4.24 mmol) in THF (25 mL). After stirring for 1 h at -78° C., the hydride reagent was quenched with EtOAc (10 mL), and the solution was slowly poured into a vigorously stirred mixture of citric acid (10%, 30 mL) and EtOAc (50 mL). After separating the layers, the organic layer was washed with NaHCO₃ (3*20 mL), water (20 mL), and brine (30 mL). The solution was dried (sodium sulfate) and the solvent was removed in vacuo, giving the title compound (813 mg, 96%) as a colorless oil which was used without further purification. ¹H-NMR (CDCl₃): δ 10.28 (s, 1H), 7.80 (m, 2H), 7.25 (m, 1H), 2.78 (s, 3H).

References:

3-Dimensional Pharmaceuticals, Inc. US2004/9995, 2004, A1

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83647-43-2 Synthesis