Hydrochloric Acid → 4-Methyl-3-nitrobenzyl methanesulfonate

Temperatur

0 °C

(4-Methyl-3-nitro-phenyl)-methanol (3.00 g, 17.95 mmol) was taken up in anhydrous DCM, under argon, and triethyl amine (5.45 g, 53.85 mmol, 7.51 mL) was added. The solution was cooled to 0° C. and methanesulfonyl chloride (2.26 g, 19.74 mmol, 1.53 mL) was added slowly via syringe. The solution was allowed to warm to room temp and stir for 12 h. The reaction mixture poured into 1N HCl and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with water, brine and dried over anhydrous magnesium sulfate. The solution was filtered and the solvent removed under reduced pressure. The product was isolated by flash chromatography. (5:1 hexane/ethyl acetate) Yield 2.00 g. 1H NMR (CDCl3, 300 MHz): δ 2.62 (s, 3H), 4.61 (s, 2H), 7.36 (d, J=8 Hz, 1H), 7.36 (d, J=8 Hz, 1H), 8.02 (s, 1H).

1. temperatureto warm to room temp
2. extractionthe aqueous layer was extracted three times with ethyl acetate
3. washThe combined organic layers were washed with water, brine
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationThe solution was filtered
6. customthe solvent removed under reduced pressure
7. customThe product was isolated by flash chromatography

ORD-Eintrag

ord-32bde081ba954d259527e036ca3c4b70

Quelldatensatz

uspto-grants-2005_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06906067B2