Hexane → Pyridine, 5-(1-bromoethyl)-2-(trifluoromethyl)-
Reaction equation
[Br:1]N1C(=O)CCC1=O.N1C=CC=CC=1.[CH2:15]([C:17]1[CH:18]=[CH:19][C:20]([C:23]([F:26])([F:25])[F:24])=[N:21][CH:22]=1)[CH3:16].CCCCCC.CCOC(C)=O>C(Cl)Cl.[Cl-].[Cl-].[Cl-].[Cl-].[Zr+4]>[Br:1][CH:15]([C:17]1[CH:18]=[CH:19][C:20]([C:23]([F:26])([F:24])[F:25])=[N:21][CH:22]=1)[CH3:16]Participants
Conditions
- Temperature
- 0 °C
Procedure
N-Bromosuccinimide (1.78 g, 0.01 mol) was added to anhydrous fresh methylene chloride (60 mL) at room temperature under an atmosphere of nitrogen. Once dissolved, the solution was cooled to 0° C. The 5-ethyl-2-trifluoromethyl-pyridine pyridine (1.75 g, 0.01 mol) was dissolved in a small amount of anhydrous methylene chloride and was added via syringe followed by zirconium tetrachloride (117 mg, 0.5 mmol). The ice bath was taken away and the mixture allowed to stir at room temperature overnight. TLC showed complete reaction (9:1, hexane:EtOAc). The reaction mixture was quenched with saturated sodium bicarbonate (25 mL). The organic layer was separated and washed with brine and dried (MgSO4). The residue was purified by column chromatography (1:20, EtOAc:Hex) to give the product, 2.04 g (80%), as a pale yellow liquid; 1H NMR (CDCl3) δ 8.77 (s, 1H), 7.97 (d, 1H), 7.69 (d, 1H), 5.21 (q, 1H), 2.08 (d, 3H).
Workup
- dissolutionOnce dissolved
- additionwas added via syringe
- customThe reaction mixture was quenched with saturated sodium bicarbonate (25 mL)
- customThe organic layer was separated
- washwashed with brine
- dry with materialdried (MgSO4)
- customThe residue was purified by column chromatography (1:20, EtOAc:Hex)
- customto give the product, 2.04 g (80%)
Sources & evidence
- ORD record
- ord-4c0f2bc480d3404b89808f4119da9376
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07705154B2
Reaction notes
Loading…