Pyridine → Carbonic acid chloromethyl ester 2-fluoro-1,1-dimethylethyl ester

Under nitrogen atmosphere, to a mixture of 1-fluoro-2-methylpropane-2-ol (THF solution, 5.25 g) [CAS No. 353-80-0](Biorg. Med. Chem., volume 19, page 1580, 2011), THF (95 ml) and chloromethyl chloroformate (7 ml), pyridine (6.4 ml) was added dropwise at −78° C. The resulting mixture was stirred overnight at room temperature, and then ethyl acetate (200 mL) and heptane (200 mL) were added to the mixture. The resulting mixture was sequentially washed with 0.5 N hydrochloric acid (300 mL), saturated aqueous sodium hydrogen carbonate solution (200 mL), water (200 mL), and saturated aqueous sodium chloride solution (200 mL), and dried over anhydrous magnesium sulfate. The resulting mixture was filtered, and the filtrate obtained was concentrated under reduced pressure. The residue obtained was distilled under reduced pressure to obtain the captioned compound (5.25 g).

1. washThe resulting mixture was sequentially washed with 0.5 N hydrochloric acid (300 mL), saturated aqueous sodium hydrogen carbonate solution (200 mL), water (200 mL), and saturated aqueous sodium chloride solution (200 mL)
2. dry with materialdried over anhydrous magnesium sulfate
3. filtrationThe resulting mixture was filtered
4. customthe filtrate obtained
5. concentrationwas concentrated under reduced pressure
6. customThe residue obtained
7. distillationwas distilled under reduced pressure

ORD record

ord-e595f171379244c1b3a9faa2d298d61c

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436009B2