Diisobutylaluminum hydride → (5-Bromo-2-chlorophenyl)methanol

Temperature

-78 °C

To a solution of ethyl 5-bromo-2-chlorobenzoate (1 eq.) in THF (0.03 M) was added, at −78° C., DIBAL (2.5 eq). The reaction was stirred at −78° C. for 1 h and then warmed slowly to RT over 1 h. The reaction mixture was then diluted with ether and carefully quenched with aq. 6 M HCl. The organic layer was separated and the aqueous layer was back extracted with ether. The combined organic extracts were washed with sat. aq. NaHCO3 and brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded a white semi-solid. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 3:1 (v/v) Hex:EtOAc) afforded the title compound as a light yellow oil.

1. temperaturewarmed slowly to RT over 1 h
2. customcarefully quenched with aq. 6 M HCl
3. customThe organic layer was separated
4. extractionthe aqueous layer was back extracted with ether
5. washThe combined organic extracts were washed with sat. aq. NaHCO3 and brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. customConcentration of the filtrate in vacuo afforded a white semi-solid
9. customPurification of the crude product
10. customthus obtained by way of flash chromatography (SiO2, 3:1 (v/v) Hex:EtOAc)

ORD record

ord-418bef0454054759b6f3b7902923040e

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08063105B2