Benzoyl Peroxide → HCID 131726712, compound

HRID 969620Notes

Reaction equation

HRID 969620 reaction equation
I[C:2]([C:5]([O:8][C:9]([C:12]([S:15]([F:18])(=[O:17])=[O:16])([F:14])[F:13])([F:11])[F:10])([F:7])[F:6])([F:4])[F:3].[Si:19]([CH:26]=[CH2:27])([O:24][CH3:25])([O:22][CH3:23])[O:20][CH3:21].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>N#N>[Si:19]([CH2:26][CH2:27][C:2]([C:5]([O:8][C:9]([C:12]([S:15]([F:18])(=[O:17])=[O:16])([F:14])[F:13])([F:11])[F:10])([F:7])[F:6])([F:4])[F:3])([O:24][CH3:25])([O:22][CH3:23])[O:20][CH3:21]

Participants

5

Reactant 3

HCID 7187Benzoyl Peroxide2×HCID 76004VinyltrimethoxysilaneHCID 27751695-Iodoperfluoro-3-oxapentanesulfonyl fluoride

Product 1

HCID 131726712HCID 131726712, compound

Reagents, catalysts & solvents 1

HCID 947NitrogenSolvent

Conditions

Temperature
95 °C

Procedure

Following the teachings of Beckerbauer et al, op.cit., U.S. Pat. No. 5,958,822, (CH3O)3SiCH2CH2CF2CF2OCF2CF2SO2F was prepared as follows. To a stirred mixture of 85 g (0.2 mol) of ICF2CF2OCF2CF2SO2F available from the Shanghai Institute of Organic Chemistry, Shanghai, China, and 32 g (0.215 mol) of (CH3O)3SiCH═CH2 (Aldrich Chemical Company) was added 0.5 g of benzoyl peroxide (Aldrich) at 90 to 95° C. in N2 and the resulting mixture was stirred at 95° C. for 40 minutes. An additional 0.5 g of benzoyl peroxide was added and the mixture was stirred for 4 hours more and then evacuated to remove excess starting materials. After the mixture was cooled to room temperature, 59 g of (C4H9)3SnH was slowly added and the mixture was stirred at room temperature overnight and distilled to give 60.9 g of liquid (CH3O)3SiCH2CH2CF2CF2OCF2CF2SO2F having a purity of greater than 99% and boiling point of 55° C./3 mm Hg. 19F NMR(CDCl3): +44.9 (s, 1F), −82.6 (m, 2F), −87.4 (m, 2F), −112.6 (s, 2F), −120.7 (t, J=15 Hz, 2F), 1HNMR: 3.60 (s, 9H), 2.10 (m, 2H), 0.70 (m, 2H).

Workup

  1. stirringthe mixture was stirred for 4 hours more
  2. customevacuated
  3. customto remove excess starting materials
  4. temperatureAfter the mixture was cooled to room temperature
  5. addition59 g of (C4H9)3SnH was slowly added
  6. stirringthe mixture was stirred at room temperature overnight
  7. distillationdistilled

Sources & evidence

ORD record
ord-eeccf120e35f46cf80853a611105a614
Source dataset
uspto-grants-2007_12
Patent number
US07307113B2

Reaction notes

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