Chlorotrimethylsilane → 1,8-Bis(trimethylsilyl)hexadecafluorooctane

HRID 2371598

반응식

HRID 2371598 반응식
Br[C:2]([F:26])([F:25])[C:3]([F:24])([F:23])[C:4]([F:22])([F:21])[C:5]([F:20])([F:19])[C:6]([F:18])([F:17])[C:7]([F:16])([F:15])[C:8]([F:14])([F:13])[C:9]([F:12])([F:11])Br.[CH3:27][Si:28](Cl)([CH3:30])[CH3:29].[Mg].F[C]>C1COCC1>[CH3:27][Si:28]([CH3:30])([CH3:29])[C:2]([F:26])([F:25])[C:3]([F:24])([F:23])[C:4]([F:22])([F:21])[C:5]([F:20])([F:19])[C:6]([F:18])([F:17])[C:7]([F:16])([F:15])[C:8]([F:14])([F:13])[C:9]([F:12])([F:11])[Si:28]([CH3:30])([CH3:29])[CH3:27]

참가 물질

6

반응물 4

HCID 6397ChlorotrimethylsilaneHCID 27367861,8-DibromoperfluorooctaneHCID 5462224MagnesiumHCID 178477749HCID 178477749, 화합물

생성물 1

HCID 198068601,8-Bis(trimethylsilyl)hexadecafluorooctane수율 71%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
25 °C

실험 절차

A mixture of 1,8-dibromohexadecafluorooctane (27.3 g) and the corresponding C10 derivative (4.4 g) (55.5 mmol) and trimethylsilyl chloride (54.9 g, 0.55 mol) was added to a slurry of magnesium turnings (4.11 g, 69 mmol) in THF (300 mL) over 25 minutes at -35° C. The mixture was stirred for 1.5 hours. The mixture was then allowed to warm slowly to 25° C. over 18 hours. Excess magnesium was removed by N2 pressure filtration, and most of the solvent was removed under reduced pressure. Petroleum ether (50 mL) was added, and the mixture was treated (twice) with 500 ml ice water. The organic layer was dried, stripped and kugelrohr distilled to provide 5.17 g (bp 50°-66° C., 0.05 mm; 55% of 1,8-bis(silyl) derivative, and a higher-boiling fraction, 21.4 g (bp 60°-80° C.; 82% 1,8-bis(silyl) derivative and 13% 1,10-bis(silyl) derivative; overall yield ca. 71%). 1H NMR (THF-d8): 0.30 (s). 19F NMR (THF-d8 /Freon® 11): -118.54 (s, 4F, CF2Si), -121.52 (s, 8F), -127.97 (s, 4F). GC analysis of the sample used for NMR showed a 92.4/7.6 ratio of C8 /C10 fluorocarbon products.

후처리

  1. customExcess magnesium was removed by N2 pressure filtration
  2. custommost of the solvent was removed under reduced pressure
  3. additionPetroleum ether (50 mL) was added
  4. additionthe mixture was treated (twice) with 500 ml ice water
  5. customThe organic layer was dried
  6. distillationkugelrohr distilled
  7. customto provide 5.17 g (bp 50°-66° C., 0.05 mm

출처 및 근거

ORD 기록
ord-970afe69b51f4fbb9fc29cbdc485814b
출처 데이터셋
uspto-grants-1992_03
특허 번호
US05093512

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