Triethylamine → Methyl 5-chloro-2-fluoro-4-methylbenzoate

温度

80 °C

To a solution of 1-bromo-5-chloro-2-fluoro-4-methylbenzene (10 g, 44.7 mmol) in methanol (200 mL) was added 1,1′-binaphthalene-2,2′-diylbis(diphenylphosphine)-dichloropalladium (1:1) (358 mg, 0.447 mmol) and N,N-diethylethanamine (8.11 mL, 58.2 mmol). The resulting mixture was placed in a bomb and pressurized with carbon monoxide to 80 psi and heated at 80° C. for 18 hours. The cooled reaction mixture was then concentrated in vacuo to yield a semi-solid, which was dissolved in EtOAc (300 mL) and washed with water (200 mL). The organic layer was separated, dried over magnesium sulphate, filtered and concentrated in vacuo to yield an orange oil, which solidified on standing (9.87 g). The solid was purified by silica gel column chromatography eluting with 0 to 20% EtOAc in heptane to afford the title compound as a crystalline white solid (8.47 g, 93%):

1. customThe cooled reaction mixture
2. concentrationwas then concentrated in vacuo
3. customto yield a semi-solid, which
4. washwashed with water (200 mL)
5. customThe organic layer was separated
6. dry with materialdried over magnesium sulphate
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customto yield an orange oil, which
10. customThe solid was purified by silica gel column chromatography
11. washeluting with 0 to 20% EtOAc in heptane

ORDレコード

ord-dadb30a509f74c179e2db7411ecbdf2a

出典データセット

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08592629B2