Sodium hydride → 2-Chloro-1-(3-fluoro-benzyloxy)-4-nitro-benzene

Temperature

0 °C

Sodium hydride (60% dispersion in oil, 1.4 g, 33.5 mmol) was suspended in anhydrous THF (50 ml) under nitrogen and the resulting mixture is cooled to 0° C. To above suspension was added dropwisely (3-Fluoro-phenyl)-methanol (2.90 ml, 27 mmol), followed by a solution of 2-chloro-1-fluoro-4-nitro-benzene (4.2 g, 24 mmol) in dry DMF (20 ml). The reaction mixture was then stirred at room temperature for another 4 hours. The reaction mixture concentrated under vacuum to about 40 mL, and was poured into 200 ml of ice:water. The resultant solid was isolated by filtration, washed with water (50 ml), and air dried to yield a yellow solid, 2-Chloro-1-(3-fluoro-benzyloxy)-4-nitro-benzene (5.8 g). The solid was suspended in MeOH (50 ml) and treated wet 5% Pt/C (Degussa type, Aldrich, 1.5 g). The flask is flushed with hydrogen gas from a balloon and the reaction mixture was stirred under hydrogen balloon for 2 hours. The reaction mixture was filtered through a Celite plug and the solvent is removed under reduced pressure to yield 5.2 g of the desired product.

1. concentrationThe reaction mixture concentrated under vacuum to about 40 mL
2. additionwas poured into 200 ml of ice
3. customThe resultant solid was isolated by filtration
4. washwashed with water (50 ml), and air
5. customdried

ORD record

ord-b21bbd4f5e6840189e157b97eb69dcce

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987284B2