Water → HCID 17980961, compound

HRID 2219999Notes

Reaction equation

HRID 2219999 reaction equation
Br[C:2]1[C:3]2[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:4]=2[S:5][C:6]=1[CH3:7].[Li]CCCC.[F:19][C:20]1[C:24]([F:26])([F:25])[C:23]([F:28])([F:27])[C:22]([F:30])([F:29])[C:21]=1F.O>C1COCC1.CCCCCC>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:3]2[C:2]([C:21]3[C:22]([F:30])([F:29])[C:23]([F:27])([F:28])[C:24]([F:25])([F:26])[C:20]=3[F:19])=[C:6]([CH3:7])[S:5][C:4]=2[CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11212PerfluorocyclopenteneHCID 17980974HCID 17980974, compoundHCID 178418339Butyllithium

Product 1

HCID 17980961HCID 17980961, compoundYield 73.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 7.61 g (0.03 mol) of 3-Bromo-6-methoxy-2-methylbenzo[b]thiophene (compound obtained in Step 2 of the synthesis of the compound 9) in 120 mL of anhydrous THF is added dropwise 11.90 mL (0.034 mol) of a 2.5M solution of nBuLi in hexane at −78° C. under nitrogen atmosphere. The resulting mixture is stirred for 30 min at −78° C., then 20 g (0.09 mol) of perfluorocyclopentene is added in a single portion. After the addition is completed, the mixture is allowed to return to room temperature, then hydrolysed with 120 mL of water. The mixture THF-water is extracted three times with 150 mL of Et2O. The resulting organic phase is washed several times with saturated aqueous NaCl solution, dried over magnesium sulfate and then concentrated under reduced pressure. The crude product purified by column chromatography on silica gel and eluted with mixtures consisting of pentane and CH2Cl2 of increasing polarity (100:0 to 80:20) gives an oily product (8.12 g, 72% yield), pure enough to be used in the next step without further purification.

Workup

  1. additionAfter the addition
  2. customto return to room temperature
  3. extractionThe mixture THF-water is extracted three times with 150 mL of Et2O
  4. washThe resulting organic phase is washed several times with saturated aqueous NaCl solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product purified by column chromatography on silica gel
  8. washeluted with mixtures
  9. temperatureof increasing polarity (100:0 to 80:20)

Sources & evidence

ORD record
ord-13e4c508c2e240089cc47144cec735bb
Source dataset
uspto-grants-2008_08
Patent number
US07416682B2

Reaction notes

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