HCID 67266122, compound → HCID 57816586, compound

Participants

Reaction Steps

PCC (9.29 g, 43.1 mmol) was admixed with 9 g SiO2 and ground with mortar & pestle before being added in one portion to a solution of 1-(4-bromophenyl)-5,5,5-trifluoropentan-1-ol (6.4 g, 21.54 mmol) dissolved in dichloromethane (350 mL). The reaction was stirred 4 h, filtered through diatomaceous earth (Celite®), concentrated, and applied to a 160 g Thomson® silica gel column. Elution: 10-60% B over 1.5 L (A/B Hexanes/EtOAc) gave Example 5b, 1-(4-bromophenyl)-5,5,5-trifluoropentan-1-one 6.1 g (86%). 1H NMR (500 MHz, CDCl3) δ 7.81 (d, J=8.5 Hz, 2H), 7.61 (d, J=8.3 Hz, 2H), 3.04 (t, J=7.0 Hz, 2H), 2.25-2.16 (m, 2H), 2.05-1.99 (m, 2H). RT=2.1 minutes (condition 1). LCMS: Anal. Calcd. For C11H11BrF3O: 295.00. found: 295.00 (M+H).

Provenance & Evidence