Sodium Iodide → 1-(3-Nitro-4-phenylmethoxyphenyl)ethanone

温度

20 °C

To a mechanically stirred DMF (260 mL) suspension of 1-[4-hydroxy-3-nitrophenyl]ethanone (51 g, 282 mmol) and K2CO3 (17 g, 847 mmol) was added benzyl bromide (68 mL, 572 mmol) followed by NaI (47 g, 313 mmol). After stirring overnight at 20° C., an additional 10 mL of benzyl bromide was added and the reaction was stirred for 15 more minutes. The reaction was quenched by the addition of 1.6 L water. The resulting suspension was stirred overnight and then filtered. The collected solids were washed 3×250 mL=750 mL water and dried in vacuo at ~55° C. to give 75 g crude product which was slurried in 1.3 L toluene at ~75° C., filtered hot through a 5.0 μm membrane, concentrated in vacuo to a volume of ~300 mL, diluted with 250 mL heptane, and the suspension cooled from ~60° C. to ambient. After filtration, the collected solids were washed with heptane and dried in vacuo at ~55° C. to give 64 g (84%) of the title compound.

1. stirringthe reaction was stirred for 15 more minutes
2. customThe reaction was quenched by the addition of 1.6 L water
3. stirringThe resulting suspension was stirred overnight
4. filtrationfiltered
5. washThe collected solids were washed 3×250 mL=750 mL water
6. customdried in vacuo at ~55° C.
7. customto give 75 g crude product which
8. filtrationfiltered hot through a 5.0 μm membrane
9. concentrationconcentrated in vacuo to a volume of ~300 mL
10. additiondiluted with 250 mL heptane
11. temperaturethe suspension cooled from ~60° C.
12. filtrationAfter filtration
13. washthe collected solids were washed with heptane
14. customdried in vacuo at ~55° C.

ORDレコード

ord-a1277345ecd2461dafe9eaf0610e5c60

出典データセット

uspto-grants-1998_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05770615