Thionyl Chloride → HCID 13154747, compound

HRID 325866Notes

Reaction equation

HRID 325866 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:16]3[C:11](=[CH:12][C:13]([F:17])=[CH:14][CH:15]=3)[CH:10](O)[CH2:9]2)=[CH:4][CH:3]=1.S(Cl)([Cl:21])=O>C1(C)C=CC=CC=1>[Cl:21][CH:10]1[C:11]2[C:16](=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[CH:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:9]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 13154732HCID 13154732, compound

Product 1

HCID 13154747HCID 13154747, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 52 grams of 3-(4'-fluorophenyl)-6-fluoro-1-indanol in 250 milliliters of dry toluene was cooled in ice water, and a solution of 21 milliliters of thionylchloride in 21 milliliters of toluene was added dropwise keeping the reaction temperature below 10 degrees Centigrade. The reaction mixture was stirred at room temperature for 30 minutes and then slowly heated to 60 degrees Centigrade in a water-bath and kept at this temperature for one hour. The reaction mixture was then treated with ice-water, extracted with an aqueous sodium carbonate solution and dried over anhydrous magnesium sulfate. After filtration and evaporation in vacuo there was obtained 55 grams of crude 1-chloro-3-(4'-fluorophenyl)-6-fluoroindane, which was used in the next step without further purification.

Workup

  1. customthe reaction temperature below 10 degrees Centigrade
  2. temperatureslowly heated to 60 degrees Centigrade in a water-bath
  3. waitkept at this temperature for one hour
  4. extractionextracted with an aqueous sodium carbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtration and evaporation in vacuo

Sources & evidence

ORD record
ord-ce5ce3c58aa5498aad6ffd24d5ef3033
Source dataset
uspto-grants-1984_04
Patent number
US04443448

Reaction notes

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