Toluene → Methyl 2-fluoro-4-methylbenzoate

To a solution of 2-fluoro-4-methylbenzoic acid from Example D1 (6.04 g, 39.18 mmol) in toluene (80 ml) was added thionyl chloride (6.5 ml, 89.11 mmol). The mixture was heated at reflux for 2.5 h, cooled and concentrated in vacuo. The residue was dissolved in dichloromethane (50 ml) and methanol (50 ml) was added. The mixture was stirred at room temperature for 2.5 h and then concentrated in vacuo. The residue was dissolved in dichloromethane (100 ml), washed with saturated sodium bicarbonate solution and brine, dried over MgSO4, and concentrated in vacuo to give a tan solid; yield 5.07 g (77%).

1. temperatureThe mixture was heated
2. temperatureat reflux for 2.5 h
3. temperaturecooled
4. concentrationconcentrated in vacuo
5. dissolutionThe residue was dissolved in dichloromethane (50 ml)
6. additionmethanol (50 ml) was added
7. concentrationconcentrated in vacuo
8. dissolutionThe residue was dissolved in dichloromethane (100 ml)
9. washwashed with saturated sodium bicarbonate solution and brine
10. dry with materialdried over MgSO4
11. concentrationconcentrated in vacuo
12. customto give a tan solid

ORD record

ord-3100b794720c4c49828dfadceb156a75

Source dataset

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06664249B1