Triethylamine → CH2=C(CF3)CF2OC6F5

HRID 1178840Notes

Reaction equation

HRID 1178840 reaction equation
[F:1][C:2]1[C:7]([OH:8])=[C:6]([F:9])[C:5]([F:10])=[C:4]([F:11])[C:3]=1[F:12].C(N(CC)CC)C.[CH2:20]=[C:21]([C:26](OS(F)(=O)=O)([F:28])[F:27])[C:22]([F:25])([F:24])[F:23]>C(OCC)C>[CH2:20]=[C:21]([C:26]([O:8][C:7]1[C:6]([F:9])=[C:5]([F:10])[C:4]([F:11])=[C:3]([F:12])[C:2]=1[F:1])([F:28])[F:27])[C:22]([F:25])([F:24])[F:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13041PentafluorophenolHCID 87741755CH2=C(CF3)CF2Oso2F

Product 1

HCID 85887664CH2=C(CF3)CF2OC6F5Yield 74.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
20 °C

Procedure

Pentafluorophenol (7.5 g, 0.040 mole) and triethylamine (4.5 g, 0.044 mole) in dry ethyl ether (7 ml) are added gradually to CH2═C(CF3)CF2OSO2F (11 g, 0.045 mole) in ethyl ether (14 ml) at 20° C. The reaction mixture is agitated at 20° C. for 30 minutes and washed in turn with water, dilute aqueous HCl, water, sodium bicarbonate solution, and water and the resulting ether solution is dried over MgSO4. Distillation of the dried mixture gives CH2═C(CF3)CF2OC6F5 (9.8 g, 73% yield, b.pt. 86–88° C. at 20 mm Hg).

Workup

  1. washwashed in turn with water, dilute aqueous HCl, water, sodium bicarbonate solution, and water
  2. dry with materialthe resulting ether solution is dried over MgSO4
  3. distillationDistillation of the dried mixture

Sources & evidence

ORD record
ord-230b0ba6d6ef4c68bfe86b1f87a80caa
Source dataset
uspto-grants-2007_10
Patent number
US07276624B2

Reaction notes

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