Potassium Bromide → HCID 54208139, compound

Participants

Reaction Conditions

Reaction Steps

TEMPO (0.02 equiv, 6 mg, 0.038 mmol) was added to a solution of methyl 2-(4-(3-hydroxypropyl)phenyl)acetate in CH2Cl2 (5 mL) and cooled to 0° C. KBr (2.2 equiv, 1.6 mL, 2.7M) and KHCO3 (5.5 equiv, 6.6 mL, 1.6M) solutions were then added followed by the dropwise addition of 10% aq. NaOCl (1.34 equiv, 1.9 g, 2.6 mmol). Once the addition was complete, the reaction was stirred for an additional 10 min. at 0° C. The reaction was quenched with sat. aq. sodium thiosulfate solution (3 mL) and then partitioned between H2O (10 mL) and CH2Cl2 (10 mL). The organic phase was separated and the remaining aqueous phase was extracted with EtOAc (2×2 mL). The organic layers were combined, dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting aldehyde was carried forward to the subsequent reaction without further purification. LRMS: 206.1 (calc) 207.2 (found)(MH)+.

Provenance & Evidence