Water → Methyl 2-chloro-6-fluorobenzoate

An oven-dried round bottom flask successively purged and evacuated with N2 was charged with anhydrous 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 1-chloro-3-fluorobenzene (5.48 g, 42.0 mmol) neat. 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 followed by EtOAc. The layers were separated and the aqueous layer was extracted three times with 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 purged
2. customevacuated with N2
3. additionwas charged with anhydrous 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 three times with EtOAc
8. washThe combined organics were washed with brine
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. concentrationconcentrated

ORD record

ord-7e501142445e43b6828d7cf3c6a88846

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08163742B2