Tetrahydrofuran → 4-Bromo-2-methoxy-6-methylbenzaldehyde

To a solution of 4-bromo-2-methoxy-6-methyl-benzonitrile (2.8 g, 12.38 mmol) in tetrahydrofuran (24.8 ml) is added diisobutylaluminium hydride (1.2 M in toluene) (24.8 ml, 29.7 mmol) at −78° C. The reaction mixture is slowly warmed to RT and stirred at RT for 18 h. The reaction is quenched with 1 M hydrochloric acid at 0° C. The resulting mixture is stirred at RT for 1 h and extracted with ethyl acetate (3×50 ml). The combined organic layers are washed with water (40 ml), dried over sodium sulfate and evaporated. The crude product is purified by column chromatography (silica gel, 1.5% ethyl acetate/hexane) yielding 4-bromo-2-methoxy-6-methyl-benzaldehyde (1.25 g, 5.45 mmol, 44%).

1. customThe reaction is quenched with 1 M hydrochloric acid at 0° C
2. stirringThe resulting mixture is stirred at RT for 1 h
3. extractionextracted with ethyl acetate (3×50 ml)
4. washThe combined organic layers are washed with water (40 ml)
5. dry with materialdried over sodium sulfate
6. customevaporated
7. customThe crude product is purified by column chromatography (silica gel, 1.5% ethyl acetate/hexane)

ORD record

ord-5ee3711efb5940bab37aa89c56ee628f

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09108936B2