1,1'-Carbonyldiimidazole → 4-Bromo-2-fluoro-6-methylbenzamide

4-bromo-2-fluoro-6-methyl benzoic acid (200 g) was dissolved in 1 L of THF and treated portion wise with carbonyldiimidazole (180 g, 1.3 eq). The reaction mixture is stirred at ambient temperature for about 3 hours and then quenched by addition of aqueous ammonium hydroxide (400 ml). The resulting reaction mixture was stirred overnight at ambient temperature and then concentrated under reduced pressure to about 0.5 L volume. The resulting slurry was diluted by adding 1 L of water. The precipitated product was isolated by filtration, washed with water (3×300 ml), dried under vacuum at about 60° C. to obtain 174 g (87% isolated yield) of product.

1. customquenched by addition of aqueous ammonium hydroxide (400 ml)
2. customThe resulting reaction mixture
3. stirringwas stirred overnight at ambient temperature
4. concentrationconcentrated under reduced pressure to about 0.5 L volume
5. additionThe resulting slurry was diluted
6. additionby adding 1 L of water
7. customThe precipitated product was isolated by filtration
8. washwashed with water (3×300 ml)
9. customdried under vacuum at about 60° C.
10. customto obtain
11. custom174 g (87% isolated yield) of product

ORDレコード

ord-71c449bf75f24e2c975af0f34bd83e75

出典データセット

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08299077B2