Hydrochloric Acid → 2-Propen-1-ol, 3-(4-bromophenyl)-, (2E)-

Temperatur

-78 °C

To a solution of ethyl trans-4-bromocinnamate [CAS 24393-53-1] (8 mL, 42.6 mmol) in anhydrous dichloromethane (150 mL) under N2 was added dropwise diisobutylaluminum hydride in dichloromethane (128 mL, 1M, 128 mmol) at −78° C. Following the addition, the mixture was allowed to warm from −78° C. to −30° C. over two hours. The mixture was then cooled back to −78° C. and aqueous 1 N HCl was added. The organic layer was separated, dried with MgSO4, filtered and concentrated under reduced pressure to provide the title compound. 1H NMR (300 MHz, CDCl3): δ 1.44 (t, J=6 Hz, 1H), 4.32 (t, J=4.5 Hz, 2H), 6.37 (dt, J=16.5 Hz, J=6 Hz, 1H), 6.57 (dt, J=15 Hz, J=3 Hz, 1H), 7.25 (d, J=9 Hz, 2H), 7.45 (d, J=9 Hz, 2H). MS (DCl—NH3) m/z 214 (M+H)+.

1. additionthe addition
2. temperatureto warm from −78° C. to −30° C. over two hours
3. customThe organic layer was separated
4. dry with materialdried with MgSO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure

ORD-Eintrag

ord-bcdd3170187f49c0bb053db6c2547d0c

Quelldatensatz

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09108948B2