tert-Butyl acetate → Tert-butyl 3-(4-bromophenyl)propanoate

Temperature

-78 °C

To a solution of cyclohexyl-isopropyl-amine (1.0 eq.) in THF (2.0M) at −78° C. was added dropwise n-BuLi (0.95eq.). The mixture was stirred at −78° C. for 20 min then a solution of acetic acid tert-butyl ester (1.0 eq.) in THF (5.0M) was added dropwise. The resulting mixture was stirred at −78° C. for 1 h. A solution of 4-bromobenzyl bromide (0.9eq.) in THF (5.0M) was then added dropwise and the final mixture was warm slowly to rt and stirred for 12 h. The reaction was quenched with cold aqueous HCl (1M), diluted water and extracted with Et2O (2×). The combined organic extracts were washed with HCl (1M), brine, dried over Na2SO4, filtered and concentrated. The residue was distilled under vacuum (95° C., 0.4 mmHg) to afford the title compound as a colorless oil.

1. stirringThe resulting mixture was stirred at −78° C. for 1 h
2. stirringstirred for 12 h
3. customThe reaction was quenched with cold aqueous HCl (1M), diluted water
4. extractionextracted with Et2O (2×)
5. washThe combined organic extracts were washed with HCl (1M), brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated
9. distillationThe residue was distilled under vacuum (95° C., 0.4 mmHg)

ORD record

ord-e5c1445b9d2443cfb632602d43190219

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07153968B2