Diisobutylaluminum hydride → 4-(Bromomethyl)benzyl alcohol

Temperature

0 °C

To a solution of methyl 4-bromomethylbenzoate (5.73 g, 25 mmol) in dry CH2Cl2 (150 mL) cooled to −78° C. with stirring under nitrogen was added dropwise a solution of DIBAL-H (82.5 mL, 1.0 M solution in THF). Stirring was continued for 1.5 h at −78° C., and the reaction mixture was then allowed to warm to 0° C. and quenched with H2O. The organic layer was separated and the aqueous was extracted with CH2Cl2 (2×100 mL). The combined organic extracts were dried (MgSO4) and evaporated to give the desired alcohol (5.0 g, 100%) as a white solid: 1H NMR (CDCl3) δ 1.84 (br, 1H), 4.49 (s, 2H), 4.67 (s, 2H), 7.33 (d, 2H, J=8.2 Hz), 7.38 (d, 2H, J=8.2 Hz).

1. stirringStirring
2. customquenched with H2O
3. customThe organic layer was separated
4. extractionthe aqueous was extracted with CH2Cl2 (2×100 mL)
5. dry with materialThe combined organic extracts were dried (MgSO4)
6. customevaporated

ORD record

ord-0cd7532805b04297a7ffbd5ef1cbf312

Source dataset

uspto-grants-2005_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06872714B1