Carbon Dioxide → Triethyl(trifluoromethyl)silane

HRID 231322노트

반응식

HRID 231322 반응식
Cl[Si:2]([CH2:7][CH3:8])([CH2:5][CH3:6])[CH2:3][CH3:4].C(=O)=O.Br[C:13]([F:16])([F:15])[F:14].C(N(CC)P(N(CC)CC)N(CC)CC)C>CC(C)=O.ClCCl>[CH2:3]([Si:2]([CH2:7][CH3:8])([CH2:5][CH3:6])[C:13]([F:16])([F:15])[F:14])[CH3:4]

참가 물질

7

반응물 4

HCID 280Carbon DioxideHCID 6384BromotrifluoromethaneHCID 13819ChlorotriethylsilaneHCID 75292Hexaethylphosphorous triamide

생성물 1

HCID 4204914Triethyl(trifluoromethyl)silane수율 69%

시약·촉매·용매 2

HCID 180Acetone용매HCID 6344Dichloromethane용매

반응 조건

온도
-78 °C

실험 절차

A flask equipped with a dry ice condenser was flame dried under a nitrogen stream, and charged with 25 g (0.17 mol) of chlorotriethylsilane and 40 mL of dichloromethane. After cooling the resulting solution to -78° C. and charging the condenser with dry ice and acetone, 40 mL (0.43 mol) of bromotrifluoromethane (Freon 13B1) that had been condensed into a graduated tube was warmed to room temperature and allowed to distill into the flask. The cold solution was treated dropwise with 66mL (0.24 mol) of hexaethylphosphorous triamide, allowed to stir at -78° C. for two hours, and allowed to stir at room temperature overnight. Low boiling components were then short path distilled into a cold (-78° C.) receiving flask at >1 torr with the pot temperature kept at <50° C. The distillate was further fractionated by removal of the dichloromethane (40°-45° C. at atmospheric pressure) and short path distillation to give 22.0 g of 98% pure (69% yield) triethyltrifluoromethylsilane: bp 52°-54° C. at 10 torr; 1H NMR (CDCl3) δ 0.59-1.16 (m); 19F NMR (CDCl3, relative to CFCl3) - 61.3 ppm (s); IR (neat) 2960, 2915, 2882, 1458, 1413, 1206, 1055, 1020, 734, 693 cm-1 ; mass spectrum (70 eV) m/z (relative intensity) 115 (66, M-CF3), 105 (46), 87 (85), 77 (100), 59 (56), 49 (41), 47 (37), 41 (38). Anal. Calcd. for C7H15F3Si: C, 45.62; H, 8.20. Found: C, 47.53; H, 8.56.

후처리

  1. customA flask equipped with a dry ice condenser
  2. temperaturewas flame
  3. customdried under a nitrogen stream
  4. customcondensed into a graduated tube
  5. temperaturewas warmed to room temperature
  6. distillationto distill into the flask
  7. stirringto stir at room temperature overnight
  8. distillationshort path distilled into a cold (-78° C.)
  9. customkept at <50° C
  10. customThe distillate was further fractionated by removal of the dichloromethane (40°-45° C. at atmospheric pressure) and short path distillation

출처 및 근거

ORD 기록
ord-aee0b6bfa15c4b53b73aa6b1c69d7eff
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04845258

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