Diethyl Ether → 4-Bromo-2-fluoro-alpha,alpha-dimethylbenzenemethanol

To a solution of methyl 4-bromo-2-fluorobenzoate (12 g, 51.5 mmol) in anhydrous ether (140 mL) at 0° C. was added MeMgBr (3.0 M, 70 g) dropwise. The mixture was slowly warmed up to room temperature and stirred for 3 hours. The reaction was quenched by the addition of saturated NH4Cl and extracted with EtOAc (3×150 mL). The combined organic extracts were washed with brine, dried with Na2SO4 and evaporated to dryness. The mixture was purified by flash column chromatography (0–20% EtOAc in hexanes) to give the product (12 g, 95% yield). 1H NMR (300 MHz, CDCl3) δ: 1.62 (s, 6 H), 7.18–7.23 (m, 1 H), 7.25–7.28 (m, 1 H), 7.44–7.49 (m, 1 H).

1. customThe reaction was quenched by the addition of saturated NH4Cl
2. extractionextracted with EtOAc (3×150 mL)
3. washThe combined organic extracts were washed with brine
4. dry with materialdried with Na2SO4
5. customevaporated to dryness
6. customThe mixture was purified by flash column chromatography (0–20% EtOAc in hexanes)

ORD record

ord-04f2e5bbf9c847c0bda52985cc0ca54e

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07148226B2