Triethylamine → 2,2,3,3-Tetrafluorocyclobutyl isopropyl ether

HRID 1534277Notes

Reaction equation

HRID 1534277 reaction equation
[CH:1]([O:4][C:5]1[C:8]([F:10])([F:9])[C:7]([F:12])([F:11])[C:6]=1Cl)([CH3:3])[CH3:2].C(N(CC)CC)C.[Cl-].[Ca+2].[Cl-]>[C].[Pd].CCOCC>[CH:1]([O:4][CH:5]1[CH2:6][C:7]([F:11])([F:12])[C:8]1([F:9])[F:10])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 5284359Calcium ChlorideHCID 199110632-Chloro-3,3,4,4-tetrafluorocyclobutenyl isopropyl ether

Product 1

HCID 199110622,2,3,3-Tetrafluorocyclobutyl isopropyl ether

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

To 40 g of 10% strength palladium-carbon under nitrogen a solution of 274 g (1.26 mol) of 2-chloro-3,3,4,4-tetrafluorocyclobutenyl isopropyl ether, 252 g (2.50 mol) of triethylamine, and 1200 ml of ether dried over calcium chloride is added, and the mixture is hydrogenated in a 3 l VA autoclave at 100° C. until the pressure is constant (about 5 hours). The solid is filtered off with suction and washed well with ether, and the filtrate is washed with dilute hydrochloric acid. After drying, the organic phase is distilled.

Workup

  1. additionis added
  2. customis hydrogenated in a 3 l VA autoclave at 100° C. until the pressure
  3. custom(about 5 hours)
  4. filtrationThe solid is filtered off with suction
  5. washwashed well with ether
  6. washthe filtrate is washed with dilute hydrochloric acid
  7. customAfter drying
  8. distillationthe organic phase is distilled

Sources & evidence

ORD record
ord-661bf16ceace454b89ab8a6f9586ea72
Source dataset
uspto-grants-1992_02
Patent number
US05087775

Reaction notes

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