Hydrogen Peroxide → HCID 66700151, compound

Borane-THF complex (36.5 mL, 1M THF, 36.5 mmol) was added to a stirred solution of 2,6-dibromo-9-methylene-9H-xanthene (9-1) (6.43 g, 18.27 mmol) in THF (75 mL) at 0° C. The mixture was allowed to warm up to rt and stirred for 1 h. The reaction mixture was cooled to 0° C. and a mixture of hydrogen peroxide (35 wt % in water) (5.76 mL, 65.8 mmol) and NaOH (25.6 mL, 2 M aq, 51.1 mmol) was added cautiously. The mixture was allowed to warm up to rt over 30 min. The reaction mixture was then poured into water (200 mL) and extracted with DCM (3×150 mL). The combined organics were washed with water (2×200 mL), brine (200 mL), dried over MgSO4, filtered and volatiles removed in vacuo to give a yellow solid. The crude product was purified by column chromatography (SiO2, 0-100% EtOAc/isohexanes) to afford (2,6-dibromo-9H-xanthen-9-yl)methanol (10-1) (2.5 g, 37.0% yield) as a yellow solid. 1H NMR (CDCl3) δ 7.42-7.39 (1H, m), 7.37-7.35 (1H, m), 7.28-7.27 (1H, m), 7.25-7.21 (1H, m), 7.16-7.12 (1H, m), 7.00-6.97 (1H, m), 4.00 (1H, t, J=5.9 Hz), 1.46 (2H, d, J=5.9 Hz) ppm.

1. temperatureThe reaction mixture was cooled to 0° C.
2. additionwas added cautiously
3. temperatureto warm up to rt over 30 min
4. extractionextracted with DCM (3×150 mL)
5. washThe combined organics were washed with water (2×200 mL), brine (200 mL)
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. customvolatiles removed in vacuo
9. customto give a yellow solid
10. customThe crude product was purified by column chromatography (SiO2, 0-100% EtOAc/isohexanes)

ORD record

ord-fa3b66557d8e488ca6f1556deaa11be0

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09150554B2