tert-Butanol → Tert-butyl 3-bromobutanoate

3-{2-[4-(2,6-Dichloro-benzyloxy)-phenyl]-morpholin-4-yl}-butyric acid tert-butyl ester was obtained according to a similar manner. The required 3-bromobutyric acid tert-butyl ester was prepared as follows: To a solution of 3-bromobutyric acid (5.0 mL; 47.0 mmol) in tetrahydrofuran (50 mL) was added dropwise trifluoroacetic anhydride (13.7 mL; 98.7 mmol) at −40° C. After 1 hour at −40° C. tert-butyl alcohol (20 mL) was added. The resulting mixture was allowed to warm to RT and stirred overnight. Subsequently, the reaction mixture was concentrated in vacuo. The residue was treated with 2M aqueous NaOH solution and extracted with Et2O. The organic layer was dried (Na2SO4), and concentrated in vacuo to afford 3-bromobutyric acid tert-butyl ester (6.05 g), which was used as such.

1. customThe required 3-bromobutyric acid tert-butyl ester was prepared
2. concentrationSubsequently, the reaction mixture was concentrated in vacuo
3. additionThe residue was treated with 2M aqueous NaOH solution
4. extractionextracted with Et2O
5. dry with materialThe organic layer was dried (Na2SO4)
6. concentrationconcentrated in vacuo

ORD record

ord-9f2230efa9b24e22b08182df5ca76526

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09273017B2