3-Fluoro-5-methylbenzyl bromide → 3-Ethyl-1-fluoro-5-methylbenzene
Reaction equation
[CH3:1][Li].Br[CH2:4][C:5]1[CH:6]=[C:7]([F:12])[CH:8]=[C:9]([CH3:11])[CH:10]=1>C(OCC)C.[Cu]I>[CH2:4]([C:5]1[CH:6]=[C:7]([F:12])[CH:8]=[C:9]([CH3:11])[CH:10]=1)[CH3:1]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Methyllithium (40 ml, 64 mmol) was added dropwise at 0° C. to a slurry of copper(I)iodide (6.42 g, 33.6 mmol) in diethyl ether (20 ml). After being stirred at 0° C. for 30 minutes, the clear colorless homogeneous cuprate solution was cooled to −78° C. where 3-bromomethyl-1-fluoro-5-methylbenzene (5.15 g, 25.4 mmol) in 10 ml diethyl ether was added. The temperature was allowed to rise slowly. The reaction was quenched at −50° C. with NH4Cl/NH3-buffer (50 ml). Extraction with diethyl ether (3×50 ml), brine (1×100 ml). The organic layer was dried over MgSO4, filtered and the solvents were removed to yield 3.3 g (94%) of the title compound.
Workup
- additionwas added
- customThe reaction was quenched at −50° C. with NH4Cl/NH3-buffer (50 ml)
- extractionExtraction with diethyl ether (3×50 ml), brine (1×100 ml)
- dry with materialThe organic layer was dried over MgSO4
- filtrationfiltered
- customthe solvents were removed
Sources & evidence
- ORD record
- ord-bf81136ac5d64f44b0beaba3638a419c
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06265415B1
Reaction notes
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