Tributylstannane → HCID 12040714, compound

HRID 963582Notes

Reaction equation

HRID 963582 reaction equation
I[CH:2]([C:12]([F:24])([F:23])[C:13]([F:22])([F:21])[C:14]([F:20])([F:19])[C:15]([F:18])([F:17])[F:16])[CH2:3][C:4]([F:11])([F:10])[C:5]([O:7][CH2:8][CH3:9])=[O:6].C([SnH](CCCC)CCCC)CCC>>[F:10][C:4]([F:11])([CH2:3][CH2:2][C:12]([F:23])([F:24])[C:13]([F:21])([F:22])[C:14]([F:19])([F:20])[C:15]([F:16])([F:18])[F:17])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

3

Reactant 2

HCID 5948TributylstannaneHCID 19082574HCID 19082574, compound

Product 1

HCID 12040714HCID 12040714, compoundYield 88%

Conditions

Temperature
50 °C

Procedure

The compound ethyl 4-iodo-2,2,5,5,6,6,7,7,8,8,8-undecafluorooctanoate prepared from Example 5 (99.2 g, 0.2 mol) was added dropwise into a well-stirred tributyltin hydride liquid (58.5 g, 0.201 mol). The reaction temperature was controlled at ~30° C. during the process. After addition was complete, the mixture was stirred at 50° C. for 2 hr. The product ethyl 2,2,5,5,6,6,7,7,8,8,8-undecafluorooctanoate (65.0 g, 88% yield) was isolated by distillation as a clear, colorless liquid having a boiling point of 38°-39° C. at 3 mmHg.

Workup

  1. customwas controlled at ~30° C. during the process
  2. additionAfter addition

Sources & evidence

ORD record
ord-e41a839060714de0b172ec7d6bf8056b
Source dataset
uspto-grants-1998_06
Patent number
US05763552

Reaction notes

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