Isopropanol → HCID 86700531, compound

HRID 625191Notes

Reaction equation

HRID 625191 reaction equation
[Br:1][C:2]([F:18])([F:17])[C:3]([CH:6]1[CH2:10][CH:9]([C:11]([OH:13])=[O:12])[CH2:8][CH:7]1[C:14]([OH:16])=[O:15])([F:5])[F:4].[CH:19](O)([CH3:21])[CH3:20].[C:23]1(C)[CH:28]=CC(S(O)(=O)=O)=C[CH:24]=1>C1CCCCC1>[Br:1][C:2]([F:17])([F:18])[C:3]([CH:6]1[CH2:10][CH:9]([C:11]([O:13][CH:19]([CH3:21])[CH3:20])=[O:12])[CH2:8][CH:7]1[C:14]([O:16][CH:23]([CH3:28])[CH3:24])=[O:15])([F:5])[F:4]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 6101p-Toluenesulfonic acidHCID 86700532HCID 86700532, compound

Product 1

HCID 86700531HCID 86700531, compoundYield 209.9%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

Into a glass flask were charged 3.00 g (8.90 mmol) of 4-(2-bromo-1,1,2,2-tetrafluoroethyl)cyclopentane-1,3-dicarboxylic acid, 25 g of isopropanol, 25 g of cyclohexane and 0.300 g of p-toluenesulfonic acid, and the mixture was refluxed using a Dean and Stark apparatus for 10 hrs. Thereafter, the solvent was distilled off, and 100 mL of ethyl acetate was added thereto. The organic layer was washed with 50 mL of an aqueous sodium bicarbonate solution three times, and then with 50 mL of saturated brine once. After washing, the solvent of the organic layer was distilled off, and purification was carried out on column chromatography to obtain 1.54 g of diisopropyl 4-(2-bromo-1,1,2,2-tetrafluoroethyl)cyclopentane-1,3-dicarboxylate (precursor compound (a-6)) represented by the following formula (a-6) (yield: 41%).

Workup

  1. temperaturethe mixture was refluxed
  2. customfor 10 hrs
  3. distillationThereafter, the solvent was distilled off
  4. addition100 mL of ethyl acetate was added
  5. washThe organic layer was washed with 50 mL of an aqueous sodium bicarbonate solution three times
  6. washAfter washing
  7. distillationthe solvent of the organic layer was distilled off
  8. custompurification

Sources & evidence

ORD record
ord-a0a084a76ad2456c9b93f7d80328e375
Source dataset
uspto-grants-2016_04
Patent number
US09304393B2

Reaction notes

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