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

Temperature

25 °C

A solution of methyl 4-bromo-2-fluorobenzoate (8.0 g, 34.3 mmol) in anhydrous Et2O (85 mL) was treated with MeMgBr (3.0 M in THF, 30 mL). The resulting solution was stirred at 25° C. for 3 hours before it was quenched by the addition of H2O (10 mL). The mixture was extracted with EtOAc (50 mL) three times and the combined organic extracts were washed with aqueous NH4Cl, brine, and dried over Na2SO4. The solvent was removed in vacuo and the residue was purified by flash column chromatography (0-25% EtOAc in hexanes) to give the desired product (7.2 g, 91% yield). 1H NMR (CDCl3, 300 MHz) δ: 1.62 (s, 6H), 7.19-7.22 (m, 1H), 7.27-7.29 (m, 1H), 7.45-7.49 (m, 1H).

1. customwas quenched by the addition of H2O (10 mL)
2. extractionThe mixture was extracted with EtOAc (50 mL) three times
3. washthe combined organic extracts were washed with aqueous NH4Cl, brine
4. dry with materialdried over Na2SO4
5. customThe solvent was removed in vacuo
6. customthe residue was purified by flash column chromatography (0-25% EtOAc in hexanes)

ORD record

ord-e7597c762e0f4f2a9d63030c5e2c6b6c

Source dataset

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07473790B2