Chlorotrimethylsilane → 1,8-Bis(trimethylsilyl)hexadecafluorooctane

HRID 2371598

反応式

HRID 2371598 の反応式
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]

参加物

6

反応物 4

HCID 6397ChlorotrimethylsilaneHCID 27367861,8-DibromoperfluorooctaneHCID 5462224MagnesiumHCID 178477749HCID 178477749、化合物

生成物 1

HCID 198068601,8-Bis(trimethylsilyl)hexadecafluorooctane収率 71%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-970afe69b51f4fbb9fc29cbdc485814b
出典データセット
uspto-grants-1992_03
特許番号
US05093512

関連ノート

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