Hydrochloric Acid → 1-Bromo-4-(2-methoxypropan-2-yl)benzene

2-(4-Bromo-phenyl)-propan-2-ol (Preparation 39, 1.77g, 8.2 mmol) and methyl iodide (0.5 mL, 8.2 mmol) in tetrahydrofuran (100 mL) were treated with sodium hydride (60% dispersion in mineral oil, 328 mg, 8.2 mmol). The mixture was stirred for 24 hours at room temperature, was poured into 0.5 M aqueous hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, was dried over magnesium sulfate, was filtered, and the solvent was removed in vacuo. The residue was purified by silica gel chromatography (200:1 hexanes-ethyl acetate) to afford 500 mg (27% yield) of the title compound. 13C NMR (100 MHz, CDCl3) d 145.4, 131.5, 127.9, 121.0, 76.7, 50.9, 28.1; MS (AP/Cl) 197.0, 199.0 (M+H—OMe)+.

1. extractionthe mixture was extracted with ethyl acetate
2. washThe organic layer was washed with brine
3. dry with materialwas dried over magnesium sulfate
4. filtrationwas filtered
5. customthe solvent was removed in vacuo
6. customThe residue was purified by silica gel chromatography (200:1 hexanes-ethyl acetate)

ORD record

ord-c74eba1043ee43c79472346bc0fa9d3e

Source dataset

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07479559B2