1,3-Diethyl 2-(4-bromophenyl)-2-methylpropanedioate → 2-(4-Bromophenyl)-2-methylpropane-1,3-diol

Temperature

0 °C

To a solution of diethyl 2-(4-bromophenyl)-2-methylmalonate (850 mg, 2.6 mmol) in dry THF (5 mL) at 0° C. was added a 1.0M solution of lithium aluminum hydride in THF (2.6 mL, 2.6 mmol). After stirring for 2 h at 0° C., the mixture was quenched by slow addition of water (5 mL). The mixture was made acidic by addition of 1N HCl and was then extracted with dichloromethane (2×20 mL). The organics were combined, dried over Na2SO4 and evaporated to give 2-(4-bromophenyl)-2-methylpropane-1,3-diol (500 mg, 79%) 1H NMR (400 MHz, DMSO-d6) δ 7.47-7.43 (m, 2H), 7.35-7.32 (m, 2H), 4.59-4.55 (m, 2H), 3.56-3.51 (m, 4H), 1.17 (s, 3H).

1. customthe mixture was quenched by slow addition of water (5 mL)
2. additionThe mixture was made acidic by addition of 1N HCl
3. extractionwas then extracted with dichloromethane (2×20 mL)
4. dry with materialdried over Na2SO4
5. customevaporated

ORD record

ord-865dfae8148d408787faaa1de4a51c91

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08846753B2