Triethylamine → 2-Chloromethyl-1-nitro-4-phenoxy-benzene

To a round bottom flask equipped with a nitrogen inlet and a water cooled condenser, 2-nitro-5-phenoxy-phenyl-methanol (2.7 g, 11.1 mmol) and triethylamine (4.7 mL, 33.9 mmol) were dissolved in dichloromethane (100 mL). Methane sulfonyl chloride (2.6 mL, 33.3 mmol) was added to the reaction mixture which was subsequently heated to reflux for 16 h. The next day the reaction was removed from the heating source, allowed to cool and poured into a separatory funnel which contained a water solution of 1N HCl. The organic phase washed 2 times with 1N HCl and one time with saturated brine solution. The phases were separated and the ethyl acetate layer was dried with sodium sulfate, filtered and the solvent removed under reduced pressure to yield a residue. The residue was purified by flash chromatography using heptanes:ethyl acetate as the mobile phase (9:1) to yield a residue.

1. customTo a round bottom flask equipped with a nitrogen inlet and a water cooled condenser
2. temperaturewas subsequently heated
3. temperatureto reflux for 16 h
4. customThe next day the reaction was removed from the heating source
5. temperatureto cool
6. additionpoured into a separatory funnel which
7. washThe organic phase washed 2 times with 1N HCl and one time with saturated brine solution
8. customThe phases were separated
9. dry with materialthe ethyl acetate layer was dried with sodium sulfate
10. filtrationfiltered
11. customthe solvent removed under reduced pressure
12. customto yield a residue
13. customThe residue was purified by flash chromatography
14. customethyl acetate as the mobile phase (9:1) to yield a residue

ORD record

ord-592a21140f784b0e96702a0fdbebfdf7

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07776882B2