Dimethyl Sulfoxide → 1,1,1-Tris(4-(2-bromotetrafluoroethoxy)phenyl)ethane

HRID 373287

反応式

HRID 373287 の反応式
CS(C)=O.[OH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[CH3:13])=[CH:8][CH:7]=1.[OH-].[K+].Br[C:31]([F:37])([F:36])[C:32]([F:35])([F:34])[Br:33]>O.C1(C)C=CC=CC=1>[Br:33][C:32]([F:35])([F:34])[C:31]([F:37])([F:36])[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][C:31]([F:37])([F:36])[C:32]([F:35])([F:34])[Br:33])=[CH:16][CH:15]=2)([C:21]2[CH:22]=[CH:23][C:24]([O:27][C:31]([F:37])([F:36])[C:32]([F:35])([F:34])[Br:33])=[CH:25][CH:26]=2)[CH3:13])=[CH:8][CH:7]=1

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 14797Potassium HydroxideHCID 313011,2-Dibromo-1,1,2,2-tetrafluoroethaneHCID 931181,1,1-Tris(4-hydroxyphenyl)ethane

生成物 1

HCID 189564651,1,1-Tris(4-(2-bromotetrafluoroethoxy)phenyl)ethane収率 12.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
35 °C

実験手順

A 1 liter 5-necked round bottom flask is fitted with a mechanical stirrer, a Dean-Stark trap topped with a nitrogen padded reflux condenser, and a thermocouple attached to a temperature controller. A mixture of DMSO (450 ml), toluene (150 ml), and 1,1,1-tris(4'-hydroxyphenyl)ethane (55.1 g, 0.18 mole) is added to the flask under nitrogen purge. After stirring for 15 minutes under a vigorous nitrogen purge, potassium hydroxide (85% pellets, 80.0 g, 1.2 mole) is slowly added to the reaction flask. The mixture is then stirred at reflux for 48 hours with azeotropic removal of water. The resulting suspension is cooled to 35° C. in an ice bath and 1,2-dibromotetrafluoroethane (155 g, 0.60 mole) is added at a rate that maintains a temperature of 30°-35° C. When the addition is complete, the mixture is heated to 50° C. with continuous stirring for 3 hours. After filtration, the solvents are removed by heating under vacuum on a rotary evaporator. The brown residue is purified by column chromatography on neutral alumina using hexane as eluent to provide as product 1,1,1-tris(4'-[2"-bromotetrafluoroethoxy]phenyl)ethane (18.3 g, 0.022 mole, 12% yield).

後処理

  1. customA 1 liter 5-necked round bottom flask is fitted with a mechanical stirrer
  2. temperaturepadded reflux condenser
  3. additionis added to the flask under nitrogen
  4. custompurge
  5. custompurge
  6. stirringThe mixture is then stirred
  7. customa temperature of 30°-35° C
  8. additionWhen the addition
  9. temperaturethe mixture is heated to 50° C.
  10. stirringwith continuous stirring for 3 hours
  11. filtrationAfter filtration
  12. customthe solvents are removed
  13. temperatureby heating under vacuum on a rotary evaporator
  14. customThe brown residue is purified by column chromatography on neutral alumina

出典と根拠

ORDレコード
ord-ac771b873a0b45f79cb051cd1480e547
出典データセット
uspto-grants-1992_11
特許番号
US05162468

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