Bromotrifluoromethane → 4-Chlorophenyl trifluoromethyl sulfide

温度

60 °C

This example illustrates the preparation of several types of perfluoroalkylsulfonylphenyl ethers. Each of these illustrated ethers are produced in (a)-(e), below. Unless otherwise indicated, the reactions described below are performed in a 250 mL, 3-necked flask equipped with a mechanical stirrer, a reflux condenser topped with a nitrogen inlet tube, and a stopper. These illustrations utilize a starting material of 1-chloro-4-(trifluoromethylsulfonyl)benzene which may be prepared as described below. First, 1-chloro-4-trifluoromethylthiobenzene is prepared as follows: ##STR11## A mixture was formed in the flask from the following materials: 73 grams (g) of 4-chlorothiophenol, 400 milliliters (mL) of dimethyl formamide (DMF), and 70 g of potassium carbonate (K2CO3). This mixture was stirred at 60° C. for one hour and cooled to ice water bath temperatures (between about 0° C. and about 5° C.) and 100 g of bromotrifluoromethane (BrCF3) was bubbled into the mixture for two hours. The mixture was then stirred for two hours while warming to room temperature (about 23° C.) and then poured into 300 mL of water with stirring to form a product. The product was extracted with 300 mL of methylene chloride, separated, and washed with 250 mL of water. The product-containing, methylene chloride phase was separated and then dried by passing it through sodium sulfate. Low boiling point (up to 100° C., unless stated otherwise) components of the product phase ("low boilers") were then distilled off under reduced pressure (about 0.5 mm Hg) and the remaining product was then distilled over a short distillation column under reduced pressure to produce an 80% yield of an oily product. The identity of the product was confirmed by gas chromatography-mass spectroscopy (GC-MS) spectra to be 1-chloro-4-trifluoromethylthiobenzene.

1. customequipped with a mechanical stirrer, a reflux condenser
2. customtopped with a nitrogen inlet tube
3. custommay be prepared
4. custom##STR11## A mixture was formed in the flask from the following materials
5. customwas bubbled into the mixture for two hours
6. stirringThe mixture was then stirred for two hours
7. temperaturewhile warming to room temperature (about 23° C.)
8. additionpoured into 300 mL of water
9. stirringwith stirring
10. customto form a product
11. extractionThe product was extracted with 300 mL of methylene chloride
12. customseparated
13. washwashed with 250 mL of water
14. customThe product-containing, methylene chloride phase was separated
15. customdried
16. customup to 100° C.
17. distillationwere then distilled off under reduced pressure (about 0.5 mm Hg)
18. distillationthe remaining product was then distilled over a short distillation column under reduced pressure

ORDレコード

ord-5f8571ecaf3a440b968b8bca620799fc

出典データセット

uspto-grants-1996_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05480568