Chlorotrifluoroethylene → HCID 91587288, compound
Reaction equation
[CH2:1]([C:7]1[CH:11]=[CH:10][S:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Cl:12][C:13]([F:17])=[C:14](F)[F:15]>>[Cl:12][C:13]([F:17])=[C:14]([C:10]1[S:9][CH:8]=[C:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH:11]=1)[F:15]Participants
Procedure
A solution of 3-hexylthiophene (30 g, 0179 mol) in anhydrous petrol (40-60 C., 100 ml) was cooled to −10 C. and diisopropylamine (freshly distilled, 18.1 g, 0179 mol) and tetramethylethylenediamine (TMEDA) (33 g, 028 mol) were added. N-BuLi (1.6M in hexanes, 113 ml, 0.18 mol) was added dropwise over 30 min at −10 C. The solution was warmed to 0 C. over 1 h, and then added via cannula to a solution of chlorotrifluorethylene at −78 C. The reaction was warmed to RT over 2 h and stirred for a further 16 h. The reaction was quenched with sat, ammonium chloride and extracted with THF (3×50 ml). The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure to afford a yellow oil (47 g). High vacuum distillation through a packed column with a reflux ratio head (0.1 mbar, 70-71 C.) afforded 13.0 g of product. Purity (HPLC) >99%. MS (EI) 264 (d, M+). 19F NMR revealed the expected signals, 1H and 13C NMR were complicated by the presence of cis/trans isomers.
Workup
- distillationand diisopropylamine (freshly distilled
- addition18.1 g, 0179 mol) and tetramethylethylenediamine (TMEDA) (33 g, 028 mol) were added
- temperatureThe solution was warmed to 0 C
- customThe reaction was quenched
- extractionammonium chloride and extracted with THF (3×50 ml)
- washThe combined organics were washed with brine
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-26c6467ca32c48ceb4878c56ffc882b9
- Source dataset
- uspto-grants-2004_11
- Patent number
- US06824706B2
Reaction notes
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