Hydrochloric Acid → 1-Ethyl-2-fluoro-4-methoxybenzene
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10](=O)[CH3:11].Cl.[H][H]>CO.[Pd]>[CH2:10]([C:3]1[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[CH:7][C:2]=1[F:1])[CH3:11]Participants
Procedure
To a solution of 1-(2-fluoro-4-methoxyphenyl)ethanone (FMAP) (13.46 g, 80 mmol) in MeOH (100 mL), 37% HCl (7.0 mL, 85 mmol) diluted with MeOH (5 mL) was added, followed by 5% Pd/C (340 mg, 0.4 mol %). The mixture was placed under 3 bar hydrogen at rt until the reaction was complete based on HPLC analysis. The mixture was cooled to room temperature and the catalyst was removed by filtration. The solvent was removed under reduced pressure, and water (100 mL) and petroleum ether were added. The organic layer was cut and washed with water (50 mL) and dried over Na2SO4. The solvent was removed under the reduced pressure. The oily residue was distilled using 8×1 cm distillation column with Raschig rings at 95-97° C. and 45 mbar to yield 1-ethyl-2-fluoro-4-methoxybenzene (MET) as a colorless oil (8.15 g, 66%). 1H NMR (CDCl3) δ 1.19 (t, J=7.6, 3H), 2.60 (q, J=7.6, 2H), 3.77 (s, 3H), 6.52-6.68 (m, 2H), 7.08 (t, J=8.6, 1 H).
Workup
- additionwas added
- customthe catalyst was removed by filtration
- customThe solvent was removed under reduced pressure, and water (100 mL) and petroleum ether
- additionwere added
- washwashed with water (50 mL)
- dry with materialdried over Na2SO4
- customThe solvent was removed under the reduced pressure
- distillationThe oily residue was distilled
- distillation8×1 cm distillation column with Raschig rings at 95-97° C.
Sources & evidence
- ORD record
- ord-eab25b69a5cb48d99f9d993b6fb68443
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09212118B2
Reaction notes
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