2-ethylphenol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2-ethylphenol (2.44 g, 20 mmol) in 80 mL of anhydrous acetonitrile was treated with nitronium tetrafluoroborate (2.93 g, 22 mmols) in portions over a period of 5 minutes at −30° C. to −40° C. After 20 minutes, the mixture was quenched with ice, treated with cold water and extracted with three 100 mL portions of dichloromethane. The combined organic layers were washed with two 30 mL portions of water, dried over sodium sulfate, filtered, and concentrated in vacuo. Chromatography on SiO2 (20% ethyl acetate in hexanes) gave 2.0 g of 2-ethyl-6-nitrophenol as a yellow oil (60% yield). the mixture was quenched with ice treated with cold water extracted with three 100 mL portions of dichloromethane The combined organic layers were washed with two 30 mL portions of water dried over sodium sulfate filtered concentrated in vacuo