Water → Methyl 2-chloro-6-fluorobenzoate

An oven-dried round bottom flask successively evacuated and purged with N2 gas was charged with drisolv THF (84 ml) and placed in a −78° C. dry ice/acetone bath. To this was added n-butyllithium (2.5 M in hexanes) (18 ml, 46 mmol) and the mixture was stirred for 10 min before adding neat 1-chloro-3-fluorobenzene (5.48 g, 42.0 mmol). The solution was stirred for 2 hrs before adding neat methyl chloroformate (4.0 ml, 50 mmol). The resultant solution was stirred at −78° C. for 3 hrs and then allowed to warm to RT. Water was added to the mixture followed by EtOAc. The layers were separated and the aqueous layer was extracted 3× EtOAc. The combined organics were washed with brine, dried over MgSO4, filtered and concentrated to give the title compound as a clear liquid.

1. customAn oven-dried round bottom flask successively evacuated
2. custompurged with N2 gas
3. additionwas charged with drisolv THF (84 ml)
4. customplaced in a −78° C.
5. stirringThe solution was stirred for 2 hrs
6. customThe layers were separated
7. extractionthe aqueous layer was extracted 3× EtOAc
8. washThe combined organics were washed with brine
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. concentrationconcentrated

ORD record

ord-4114a19df9fb45cf8d305ab27bcd89db

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07872128B2