Diisobutylaluminum hydride → HCID 68633386, compound

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence