Ammonium Chloride → HCID 69047851, compound

After a solution of 3-fluoro-2-hydroxybenzaldehyde (600 mg, 4.28 mmol) in THF (10 ml) was cooled to 0° C., a solution of vinyl magnesium chloride in THF (1.9M, 5.42 ml, 10.3 mmol) was added thereto over 5 minutes. The mixture was gradually warmed to room temperature and stirred at room temperature overnight. The mixture was cooled to 0° C. and a saturated aqueous ammonium chloride solution was added thereto at 0° C. The mixture was extracted with ethyl acetate. The organic layer was combined and successively washed with water and a saturated aqueous NaCl solution, followed by drying with anhydrous sodium sulfate. The solid was removed by filtration and the filtrate was concentrated to obtain 772 mg of 2-fluoro-6-(1-hydroxy-2-propenyl)phenol as a pale yellow oil.

1. temperatureThe mixture was cooled to 0° C.
2. customat 0° C
3. extractionThe mixture was extracted with ethyl acetate
4. washsuccessively washed with water
5. dry with materialby drying with anhydrous sodium sulfate
6. customThe solid was removed by filtration
7. concentrationthe filtrate was concentrated

ORD record

ord-ed7a6643c9aa48cf8670db95a5a95149

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07629494B2