Hydrochloric Acid → HCID 13025550, compound

To a solution of (5-bromothiophen-2-yl)methanol (460 mg, 2.38 mmol) in 5 mL anhydrous tetrahydrofuran at room temperature was added carefully hexanes-washed sodium hydride (60% in oil, 143 mg, 3.57 mmol). After stirring at room temperature for 30 minutes, methyl iodide (0.3 mL, 4.76 mmol) was added in a single portion and the reaction mixture stirred for 16 h at room temperature. The reaction mixture was poured into 20 mL of 0.2 N hydrochloric acid. Organics were extracted with 1:1 ether/hexanes (3×25 mL), washed with 30 mL each of 5% aqueous sodium bisulfite solution and brine, dried over magnesium sulfate, filtered and concentrated. The crude residue was subjected to chromatography on silica gel with gradient elution (2-3% ethyl acetate in hexanes) to give 2-bromo-5-(methoxymethyl)thiophene (439 mg, 89%) as an oil. Used without further characterization.

1. stirringthe reaction mixture stirred for 16 h at room temperature
2. extractionOrganics were extracted with 1:1 ether/hexanes (3×25 mL)
3. washwashed with 30 mL each of 5% aqueous sodium bisulfite solution and brine
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. washThe crude residue was subjected to chromatography on silica gel with gradient elution (2-3% ethyl acetate in hexanes)

ORD record

ord-841427134f52485d80a4cf104801996a

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09315495B2