Diisobutylaluminum hydride → HCID 68633386, compound

Temperature

0 °C

A solution of DIBAL-H (2 eq., 1M in toluene) in dry toluene (0.72 M) was cooled to 0° C. Then, a solution of (E5) in dry toluene (0.45 M) was added dropwise, and the resulting solution was stirred at 0° C. for 2 h. The reaction solution was quenched with a solution of 1 N HCl and the crude was extracted with EtOAc. The organic phase was washed with brine and dried (Na2SO4). The solvent was evaporated to dryness to afford [3-bromo-2-(bromomethyl)-5-fluorophenyl]methanol as a white powder, which was dissolved in DCM (1 M) at 0° C. The resulting solution was treated with 2,6-lutidine (2 eq.) and TBDMSTf (1.5 eq.). The reaction mixture was stirred at RT for 45 min. Then, the resulting solution was partitioned between water and Et2O and the organic phase was separated and dried (Na2SO4). Evaporation of the solvent gave a residue which was purified by flash column chromatography on silica, using hexane and Petroleum ether, to yield (83%) the title compound as colourless oil. 1H NMR (400 MHz, CDCl3, 300K) δ 7.15-7.12 (2H, m), 4.74 (2H, s), 4.53 (2H, s), 0.86 (9H, s), 0.04 (6H, s).

1. customThe reaction solution was quenched with a solution of 1 N HCl
2. extractionthe crude was extracted with EtOAc
3. washThe organic phase was washed with brine
4. dry with materialdried (Na2SO4)
5. customThe solvent was evaporated to dryness

ORD record

ord-6bdef212da954a6a84ecfb7bb87b4823

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08362030B2