Toluene → Methyl 2-fluoro-4-methylbenzoate

To a solution of 2-fluoro-4-methylbenzoic acid from Example E1 (6.04 g, 39.18 mmol) in toluene (80 ml) was added thionyl chloride (65 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-489dcfefe1fe487b885b2f572479017d

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07176195B2