Sodium hydride → HCID 68048091, compound

Temperature

0 °C

Methyl hydroxyacetate (0.80 g, 8.8 mmol) was dissolved in THF (10 mL) and allowed to stir at 0° C. under a nitrogen atmosphere. NaH (0.40 g, 9.6 mmol, 60% dispersion in oil) was added portionwise over approximately 5 minutes. The cooling bath was removed and the reaction mixture was allowed to warm to ambient temperature. 1-Bromo-3-(bromomethyl)benzene (2.0 g, 8.0 mmol) was added in a single portion and the resulting mixture was heated to 40° C. After 4 hours, the reaction mixture was allowed to cool to ambient temperature and partitioned between water and EtOAc. The layers were separated, and the organic layer was washed with saturated aqueous NaHCO3, brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to afford the title compound, which was carried forward without further purification. 1H NMR (600 MHz, CDCl3): δ 7.53-7.50 (m, 1H), 7.42-7.38 (m, 1H), 7.30-7.17 (m, 2H), 4.57 (s, 2H), 4.09 (s, 2H), 3.74 (s, 3H).

1. customThe cooling bath was removed
2. temperatureto warm to ambient temperature
3. temperaturethe resulting mixture was heated to 40° C
4. temperatureto cool to ambient temperature
5. custompartitioned between water and EtOAc
6. customThe layers were separated
7. washthe organic layer was washed with saturated aqueous NaHCO3, brine
8. dry with materialdried over anhydrous Na2SO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-847e4d1a2f144a92bc18dfcd234de04e

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962608B2