Diisobutylaluminum hydride → (2E)-3-(4-bromophenyl)prop-2-en-1-ol

Temperature

-78 °C

To a solution of (E)-ethyl 3-(4-bromophenyl)acrylate (25 g, 96 mmol) in DCM (300 ml) under nitrogen and cooled to −78° C. was added dropwise DIBAL-H (240 ml, 1M in DCM, 240 mmol) in about 20 minutes. The mixture was stirred at −78° C. for 2 hours. Then, the dry ice bath was removed. The reaction was diluted with DCM (500 mL), quenched with HCl (1N), and partitioned. The combined organic phases were washed with H2O, dried and concentrated under reduced pressure to provide the title compound. 1H NMR (300 MHz, CDCl3): δ 1.43 (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 (d, J=15 Hz, 1H), 7.25 (d, J=9 Hz, 2H), 7.45 (d, J=9 Hz, 2H). MS (DCI—NH3) m/z 214 (M+H)+.

1. customThen, the dry ice bath was removed
2. additionThe reaction was diluted with DCM (500 mL)
3. customquenched with HCl (1N)
4. custompartitioned
5. washThe combined organic phases were washed with H2O
6. customdried
7. concentrationconcentrated under reduced pressure

ORD record

ord-cee7874e2b6c47d19958d9052e685217

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09186353B2