Potassium Bromide → HCID 59271830, compound

Participants

Reaction Steps

To a solution of sodium bicarbonate (627 g, 74.6 mol) and potassium bromide (672 g, 56.5 mol) in water (20 L) was added 5-{[tert-butyl(dimethyl)silyl]oxy}-4-methoxy-4-methylpentan-1-ol (3.5 kg, 11.2 mol), DCM (10 L), TEMPO (17.6 g, 113 mol). The resulting mixture was cooled to <5° C. and NaOCl (13% solution, total 6.7 L, 14.6 mol) was added in portions via a funnel while maintaining the reaction temperature <5° C. The mixture was stirred 6 hours warming to ambient temperature. The organic layer was collected. The aqueous layer was extracted with 4 L DCM. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The crude material, 4.2 kg, was used in the next step without further purification. 1H NMR (300 MHz, CDCl3): δ 9.75 (t, J=1.8 Hz, 1 H); 3.43 (q, J=10.4 Hz, 2H); 3.17 (s, 3H); 2.43 (t, J=1.8 Hz, 2H); 2.02-1.65 (m, 2 H); 0.99-0.71 (s, 9H); 0.14 (s, 6H).

Provenance & Evidence