Acetonitrile → 2-(Perfluorohexyl)ethylphosphonic acid

HRID 1952414ノート

反応式

HRID 1952414 の反応式
C([O:3][P:4]([CH2:9][CH2:10][C:11]([F:29])([F:28])[C:12]([F:27])([F:26])[C:13]([F:25])([F:24])[C:14]([F:23])([F:22])[C:15]([F:21])([F:20])[C:16]([F:19])([F:18])[F:17])(=[O:8])[O:5]CC)C.Br[Si](C)(C)C.CC#N>C(Cl)Cl.CO>[F:29][C:11]([F:28])([C:12]([F:26])([F:27])[C:13]([F:24])([F:25])[C:14]([F:22])([F:23])[C:15]([F:20])([F:21])[C:16]([F:18])([F:17])[F:19])[CH2:10][CH2:9][P:4](=[O:3])([OH:8])[OH:5]

参加物

6

反応物 3

HCID 6342AcetonitrileHCID 76113BromotrimethylsilaneHCID 11070933(3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluorooctyl)phosphonic acid diethyl ester

生成物 1

HCID 537565972-(Perfluorohexyl)ethylphosphonic acid

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

(3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluorooctyl)phosphonic acid diethyl ester (0.79 g, 1.6 mmol) was dissolved in CH2Cl2 (5 ml) under N2. Bromotrimethylsilane (0.8 ml, 6.1 mmol) was added via syringe and the mixture was stirred for 6 hours. Volatiles were removed in vacuo to give a thick orange oil; this was dissolved in MeOH (20 ml) with fuming to give a yellow solution. The mixture was stirred overnight and evaporated to dryness to give a pale yellow powder. Addition of MeCN caused separation of a white solid from the yellow solution. The solid was collected by filtration, affording the desired product as a white powder. Yield 0.56 g, 1.3 mmol, 82%. Analysis found (calculated) %: C, 22.35 (22.45); H, 1.25 (1.41). 1H NMR (d6-DMSO, 400 MHz, 298 K): δ 2.35 (m, 2H), 1.73 (m, 2H). 13C{1H} NMR (d6-DMSO, 100 MHz, 298 K): δ 121-105 (m, C-F coupling unresolved), 25.13 (t, JC-F=23 Hz), 17.10 (d, JC-P=138 Hz). 31P{1H} NMR (d6-DMSO, 162 MHz, 298 K): δ 22.87. MS (FAB, m/z): 429 ([M+H]+, 100%).

後処理

  1. customVolatiles were removed in vacuo
  2. customto give a thick orange oil
  3. customto give a yellow solution
  4. stirringThe mixture was stirred overnight
  5. customevaporated to dryness
  6. customto give a pale yellow powder
  7. customseparation of a white solid from the yellow solution
  8. filtrationThe solid was collected by filtration

出典と根拠

ORDレコード
ord-e1a2641bb7be494fbecdaa3414dbcb52
出典データセット
uspto-grants-2013_03
特許番号
US08405069B2

反応ノート

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