Methanol → Methyl 2-chloro-4-methylbenzoate

Temperature

80 °C

To 4-bromo-3-chlorotoluene (4.97 g, 24.2 mmol) in dimethylformamide (25 mL) is added palladium acetate (0.54 g, 2.42 mmol), 1,3-bis(diphenylphosphino)propane (0.998 g, 2.42 mmol), triethylamine (12.5 mL) and methanol (12.5 mL). The reaction vessel is evacuated and purged three times with carbon monoxide gas. A balloon filled with carbon monoxide gas is used to maintain the carbon monoxide atmosphere. The reaction mixture is heated at 80° C. for 8 hr. The mixture is washed with water and extracted with hexanes (2×50 mL). The combined organic layers are dried over sodium sulfate, filtered, concentrated, and chromatographed with 0–3% ethyl acetate in hexanes. 1.24 g (28%) of methyl 2-chloro-4-methylbenzoate is isolated as a colorless oil.

1. customThe reaction vessel is evacuated
2. custompurged three times with carbon monoxide gas
3. additionA balloon filled with carbon monoxide gas
4. temperatureto maintain the carbon monoxide atmosphere
5. washThe mixture is washed with water
6. extractionextracted with hexanes (2×50 mL)
7. dry with materialThe combined organic layers are dried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customchromatographed with 0–3% ethyl acetate in hexanes

ORD record

ord-aee51196cc95496697f04b34ba5c4da1

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07084170B2