Hydrochloric Acid → (2E)-3-(4-bromophenyl)prop-2-en-1-ol

Temperature

-78 °C

To a solution of ethyl trans-4-bromocinnamate (8 mL, 42.6 mmol) in anhydrous dichloromethane (150 mL) under N2 was added diisobutylaluminum hydride in dichloromethane (128 mL, 1M, 128 mmol) at −78° C. dropwise. After 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 till acidic (pH=2). The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were dried with MgSO4, filtered and concentrated under reduced pressure to provide the title compound 1H NMR (300 MHz, CDCl3): 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. additionAfter the addition
2. temperatureto warm from −78° C. to −30° C. over two hours
3. customThe organic layer was separated
4. extractionthe aqueous layer was extracted with dichloromethane
5. dry with materialThe combined organic layers were dried with MgSO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure

ORD record

ord-53054ee80e6c4e6baa08b2cb0e3f98a1

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08829041B2