2,3,5,6-Tetrafluorophenol → HCID 18332211, compound

HRID 2268721Notes

Reaction equation

HRID 2268721 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[C:4]([F:10])[C:3]=1[OH:11].C([Li])CCC.Cl[CH2:18][Si:19]([O:26][CH2:27][CH3:28])([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22]>C1(C)C=CC=CC=1>[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[C:4]([F:10])[C:3]=1[O:11][CH2:18][Si:19]([O:20][CH2:21][CH3:22])([O:26][CH2:27][CH3:28])[O:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 698582,3,5,6-TetrafluorophenolHCID 84858Silane, (chloromethyl)triethoxy-HCID 178418339Butyllithium

Product 1

HCID 18332211HCID 18332211, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3.32 g (20 mmol) of 2,3,5,6-tetrafluorophenol are dissolved in 50 ml of toluene, and 8 ml of n-butyllithium (2.5 M in hexane) are added at 0° C. After warming to room temperature, the solution is stirred for a further 2 hours. Then 4.3 g of (chloromethyl)triethoxysilane (20 mmol) are added dropwise and the reaction mixture is boiled under reflux for 6 hours. The resulting suspension is filtered and the solvent is stripped off in vacuo. The pale yellow liquid which remains is subjected to fractional distillation.

Workup

  1. temperatureunder reflux for 6 hours
  2. filtrationThe resulting suspension is filtered
  3. distillationThe pale yellow liquid which remains is subjected to fractional distillation

Sources & evidence

ORD record
ord-ebfb8748caf74c449315714feedfccce
Source dataset
uspto-grants-2001_12
Patent number
US06329313B1

Reaction notes

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