Triethylamine → 1-Bromo-4-{difluoro[4-(4,4,4-trifluorobutoxy)phenoxy]methyl}benzene

温度

-55 °C

69.3 g (164 mmol) of 2-(4-bromophenyl)-5,6-dihydro-4H-1,3-dithiin-1-ium trifluoromethanesulfonate, are solubilised in 750 mL of dichloromethane. The solution is cooled down to −55° C. 53.94 g (245 mmol) of 4-(4,4,4-trifluorobutoxy)phenol and 36.5 ml (262 mmol) of triethylamine dissolved in 300 ml of dichloromethane is added to the previous solution. The solution was cooled down to −70° C. and stirred for 45 minutes. 120 ml (736 mmol) of triethylamine trihydrofluoride are added to the mixture. A solution of 8.43 ml (164 mmol) of bromine in 60 ml of dichloromethane is added at this temperature. The reaction is stirred for one hour. The reaction is quenched by addition of NaHCO3. The organic phase is washed repeatedly with water, dried over sodium sulfate, filtrated and concentrated under reduced pressure. Chromatography of the residue on 400 g silica gel using toluene: ethyl acetate 95:5 as eluent yields 42 g of 1-bromo-4-{difluoro[4-(4,4,4-trifluorobutoxy)phenoxy]methyl}benzene.

1. additionis added to the previous solution
2. temperatureThe solution was cooled down to −70° C.
3. stirringThe reaction is stirred for one hour
4. customThe reaction is quenched by addition of NaHCO3
5. washThe organic phase is washed repeatedly with water
6. dry with materialdried over sodium sulfate
7. filtrationfiltrated
8. concentrationconcentrated under reduced pressure

ORDレコード

ord-83684ea9a74e4a04be52b400ea666508

出典データセット

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09097938B2