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0 °C

A flask was charged with (5-bromo-2-((4′-chloro-2-fluoro-5-methoxy-3′-methyl-[1,1′-biphenyl]-4-yl)amino)phenyl)methanol (6.56 g, 14.55 mmol) and DCM (72.8 ml). The solution was cooled to 0° C. To the solution was added Dess-Martin Periodinane (8.02 g, 18.92 mmol) as a solid in a single portion to give a red solution. The cold bath was removed and the solution was allowed to warm to rt. After 30 min, the solution was partitioned between DCM (100 mL) and sat. aq. sodium thiosulfite (30 mL) and 1 N NaOH (20 mL). The layers were separated and the aqueous layer was extracted with DCM (2×50 mL). The combined organic layers were dried (Na2SO4) and filtered through a plug of silica. The red mother liquor was concentrated, then taken up in minimal DCM (10 mL). To the solution was added IPA (200 mL) and a brown/yellow solid precipitated, which was collected by vacuum filtration to yield 5-bromo-2-((4′-chloro-2-fluoro-5-methoxy-3′-methyl-[1,1′-biphenyl]-4-yl)amino)benzaldehyde (2.339 g, 5.21 mmol, 35.8% yield) as brown/yellow solid. (ESI) 446.1 (M−H)−.

1. customto give a red solution
2. customThe cold bath was removed
3. temperatureto warm to rt
4. customthe solution was partitioned between DCM (100 mL) and sat. aq. sodium thiosulfite (30 mL) and 1 N NaOH (20 mL)
5. customThe layers were separated
6. extractionthe aqueous layer was extracted with DCM (2×50 mL)
7. dry with materialThe combined organic layers were dried (Na2SO4)
8. filtrationfiltered through a plug of silica
9. concentrationThe red mother liquor was concentrated
10. additionTo the solution was added IPA (200 mL)
11. customa brown/yellow solid precipitated
12. filtrationwhich was collected by vacuum filtration