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): 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 (DCl—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-881fe89a6a354060a8e4471135abec13

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08829041B2