Tetrahydrofuran → HCID 22716505, compound

Temperature

0 °C

To a stirred suspension of cerium (III) chloride (4.7 g, 15.0 mmol) in tetrahydrofuran (30 mL) at 0° C. was added drop-wise a solution of 3.0 M methyl magnesium chloride in tetrahydrofuran (6.0 mL, 19 mmol). The reaction mixture was stirred at 0° C., after which a solution of 4-acetyl-2-fluorobenzonitrile (2.5 g, 15.0 mmol) in tetrahydrofuran (20 mL) was added dropwise. The reaction mixture was stirred at 0° C. for 1 hour and then quenched with 5 mL of 2N acetic acid added drop-wise. The reaction mixture was thereafter poured into water (200 mL), acidified to a pH of 2 with 2N acetic acid, and then extracted with ethyl acetate (2×200 mL). The organic extracts were combined, washed with water and brine, dried over magnesium sulfate (MgSO4), and then concentrated to give an oil. The oil product was purified using chromatography on silica gel, eluting with ethyl acetate/hexane (1:1) to yield 1.95 g of 2-fluoro-(1-hydroxy-1-methyl-ethyl)-benzonitrile final product as an oil.

1. stirringThe reaction mixture was stirred at 0° C. for 1 hour
2. customquenched with 5 mL of 2N acetic acid added drop-wise
3. additionThe reaction mixture was thereafter poured into water (200 mL)
4. extractionextracted with ethyl acetate (2×200 mL)
5. washwashed with water and brine
6. dry with materialdried over magnesium sulfate (MgSO4)
7. concentrationconcentrated
8. customto give an oil
9. customThe oil product was purified
10. washeluting with ethyl acetate/hexane (1:1)

ORD record

ord-fb299e207e204980bbb014d8f1dceaaf

Source dataset

uspto-grants-2004_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06740655B2