Pentafluoroallyl fluorosulphate → 3-Cyanotetrafluoropropionyl fluoride

HRID 232003ノート

反応式

HRID 232003 の反応式
C[N+](CC)(CC)CC.[C:9]([C:11]([F:19])([F:18])[C:12]([F:17])([F:16])[C:13]([O-])=[O:14])#[N:10].S(F)(OC(F)(F)C(F)=C(F)[F:27])(=O)=O>COCCOCCOC>[C:9]([C:11]([F:19])([F:18])[C:12]([F:17])([F:16])[C:13]([F:27])=[O:14])#[N:10]

参加物

4

反応物 2

HCID 2776028Pentafluoroallyl fluorosulphateHCID 13581304Methyltriethylammonium 3-cyanotetrafluoropropionate

生成物 1

HCID 135813143-Cyanotetrafluoropropionyl fluoride収率 29%

試薬・触媒・溶媒 1

HCID 8150Diglyme溶媒

実験手順

A solution of 53.9 g (0.2 mole) of methyltriethylammonium-3-cyanotetrafluoropropionate prepared as in Part A in 300 ml of diglyme was stirred at -10° to -5° while 46.0 g (0.20 mole) of perfluoroallyl fluorosulfate was rapidly added. The mixture was then stirred at -10° to -5° for 1 hr., and then at -5° to 0° for 4 hr. Removal of volatiles at 35° (5 mm, 6.7×10-1 kPa) through a liquid N2 trap and fractionation gave 10.0 g (29%) of 3-cyanotetrafluoropropionyl fluoride, bp 19°-20°. IR (gas phase): 2265 (CN), 1888 (COF), and 1300-1100 cm-1 (CF) with traces of CO2, SO2F2 and SiF4 present. NMR (CCl4 ; 0°); 19F 25.8 (t of t, JFF 10.1, 5.0 Hz, 1F, COF), -106.7 (d of t, JFF 5.0, 4.6 Hz, 2F, CF2CN), and -118.5 ppm (d of t, JFF 10.1, 4.6 Hz, 2F, CF2C=O).

後処理

  1. additionwas rapidly added
  2. wait, and then at -5° to 0° for 4 hr
  3. customRemoval of volatiles at 35° (5 mm, 6.7×10-1 kPa) through a liquid N2 trap

出典と根拠

ORDレコード
ord-e04d01b614104be7991277fcef4c099a
出典データセット
uspto-grants-1989_07
特許番号
US04851161

反応ノート

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