Cyanuric chloride → (5-Methoxy-2-nitrophenyl)methanol

To a suspension of cyanuric chloride (1.84 g, 1 eq) in anh. DME (60 mL) at r.t., under N2, was added NMM (1.1 mL, 1 eq). The reaction mixture was stirred for 2 min and a precipitate was formed. A solution of 5-(methyloxy)-2-nitrobenzoic acid (2.0 g, 10 mmol) in anh. DME (20 mL) was added and the reaction mixture was stirred for 4 hr. The suspension was filtered and a solution of NaBH4 (0.57 g, 1.5 eq) in water (30 mL) was added at 0° C. The reaction mixture was stirred for 20 min at 0° C. It was then diluted with Et2O (10 mL) and acidified to pH 5 by addition of sat. aq. NH4Cl. The phases were separated and the aqueous layer was extracted with Et2O (2×100 mL). The combined organic extracts were washed with sat. aq. Na2CO3 and dried over anh. Na2SO4. The solids were filtered and the solvent evaporated to dryness. The crude product was purified by flash chromatography (silica gel, cHex/EtOAc 8:2) to give the title compound (958 mg, 53%).

1. customa precipitate was formed
2. stirringthe reaction mixture was stirred for 4 hr
3. filtrationThe suspension was filtered
4. stirringThe reaction mixture was stirred for 20 min at 0° C
5. customThe phases were separated
6. extractionthe aqueous layer was extracted with Et2O (2×100 mL)
7. washThe combined organic extracts were washed with sat. aq. Na2CO3
8. dry with materialdried over anh. Na2SO4
9. filtrationThe solids were filtered
10. customthe solvent evaporated to dryness
11. customThe crude product was purified by flash chromatography (silica gel, cHex/EtOAc 8:2)

ORD-Eintrag

ord-27c2b816fe5f4e33bb5414cdf03c5a1f

Quelldatensatz

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07427630B2