Methyl 4-bromocinnamate → 3-(4-Bromophenyl)propan-1-ol

To a THF solution (0.5 M) of methyl (2E)-3-(4-bromophenyl)acrylate (1 eq.) was added, at 0° C., lithium aluminum hydride (1.0 M THF solution, 1 eq.) dropwise over a period of for 3 h. The reaction mixture was then warmed slowly to RT over 1 h. At 0° C., the reaction was carefully quenched with freshly-deoxygenated H2O. The organic layer was separated and washed with cold 10% aq. HCl. The aqueous washes were combined and back-extracted with ether. The organic extracts were then washed further with sat. aq. NaHCO3 and brine, dried over MgSO4, filtered and the filtrate concentrated in vacuo to reveal a yellow oil. Purification by way of full vacuum distillation afforded the title compound as a colorless oil.

1. customAt 0° C., the reaction was carefully quenched with freshly-deoxygenated H2O
2. customThe organic layer was separated
3. washwashed with cold 10% aq. HCl
4. extractionback-extracted with ether
5. washThe organic extracts were then washed further with sat. aq. NaHCO3 and brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationthe filtrate concentrated in vacuo
9. customPurification
10. distillationby way of full vacuum distillation

ORD record

ord-a7dd2ee5829146e99fbf1a0860f6f122

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08063105B2