1,3-Difluoro-2-nitrobenzene → 3-Fluoro-2-nitrophenol

A solution of potassium tert-butoxide (1.23 g, 11 mmol) in 25 mL of anhydrous DMSO was stirred at room temperature for 30 minutes and treated with 1,3-difluoro-2-nitrobenzene (1.59 g, 10 mmol). After 18 hours, the mixture was diluted with 150 mL of 1 N aqueous sulfuric acid and extracted with three 50 mL portions of diethyl ether. The combined organic layers were washed with water, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was dissolved in 50 mL of trifluoroacetic acid. After 30 minutes at room temperature, the mixture was concentrated in vacuo, treated with 50 mL of 1 N aqueous sodium hydroxide, and extracted with three 30 mL portions of diethyl ether. The aqueous layer was acidified with 1 N aqueous sulfuric acid and extracted with two 50 mL portions of dichloromethane. The combined dichloromethane layers were washed with water, dried over sodium sulfate, filtered, and concentrated in vacuo to give 1.3 g of 3-fluoro-2-nitrophenol as orange oil (61% yield).

1. extractionextracted with three 50 mL portions of diethyl ether
2. washThe combined organic layers were washed with water
3. dry with materialdried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. dissolutionThe residue was dissolved in 50 mL of trifluoroacetic acid
7. waitAfter 30 minutes at room temperature
8. concentrationthe mixture was concentrated in vacuo
9. additiontreated with 50 mL of 1 N aqueous sodium hydroxide
10. extractionextracted with three 30 mL portions of diethyl ether
11. extractionextracted with two 50 mL portions of dichloromethane
12. washThe combined dichloromethane layers were washed with water
13. dry with materialdried over sodium sulfate
14. filtrationfiltered
15. concentrationconcentrated in vacuo

ORD record

ord-27378aaa7dce41d1a19a4f30562ffc51

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08741897B2