Aluminium lithium hydride → 1-(4-Bromophenyl)-1H-imidazole-5-methanol

Temperature

-20 °C

To a solution of 3-(4-bromophenyl)-3H-imidazole-4-carboxylic acid ethyl ester (4) (590 mg, 2.0 mmol) in dry THF was added lithium aluminium hydride (2.4 mL, 2.4 mmol, 1.0M in THF) dropwise at −40° C. under nitrogen, and the resulting mixture slowly warmed to −20° C. over 1 h. The reaction mixture was then quenched with saturated aqueous ammonium chloride solution (3 mL) at −20° C. and diluted with ethyl acetate (40 mL). The suspension was filtered and the filtrate was washed with brine (20 mL), dried over anhydrous sodium sulphate and concentrated in vacuo to afford [3-(4-bromophenyl)-3H-imidazol-4-yl]-methanol (5). MS (ES+): m/z 253/255 (1/1) [MH+]. 1H NMR (CDCl3, 400 MHz): δ=2.25 (br s, 1H), 4.56 (s, 2H), 7.14 (s, 1H), 7.40 (d, J=8.8 Hz, 2H), 7.63 (s, 1H), 7.64 (d, J=8.8 Hz, 2H).

1. customThe reaction mixture was then quenched with saturated aqueous ammonium chloride solution (3 mL) at −20° C.
2. additiondiluted with ethyl acetate (40 mL)
3. filtrationThe suspension was filtered
4. washthe filtrate was washed with brine (20 mL)
5. dry with materialdried over anhydrous sodium sulphate
6. concentrationconcentrated in vacuo

ORD record

ord-2b03797087294a0d99f2e58bd6eedff2

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07498354B2