Water → 2-Trifluoromethyl-9-chloro-10,11-dihydrodibenzo[b,f]thiepin

HRID 261562Notes

Reaction equation

HRID 261562 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]([F:27])([F:26])[C:9]1[CH:25]=[CH:24][C:12]2[S:13][C:14]3[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:15]=3[CH2:16][CH:17](Cl)[C:11]=2[CH:10]=1.O.[OH-].[Al+3].[Li+].[OH-].[OH-].[OH-]>O1CCCC1>[F:27][C:8]([F:7])([F:26])[C:9]1[CH:25]=[CH:24][C:12]2[S:13][C:14]3[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:15]=3[CH2:16][CH2:17][C:11]=2[CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 126871182-Trifluoromethyl-9-chloro-11-chloro-10,11-dihydrodibenzo[b,f]thiepinHCID 16206110Aluminate (Al(OH)41-), lithium, (T-4)-HCID 21226445Aluminium lithium hydride

Product 1

HCID 126871202-Trifluoromethyl-9-chloro-10,11-dihydrodibenzo[b,f]thiepinYield 18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To the mixture of 0.2 g of lithium aluminum hydride and 20 ml of anydrous tetrahydrofuran was added with stirring under ice-cooling 400 mg of 2-trifluoromethyl-9-chloro-11-chloro-10,11-dihydrodibenzo[b,f]thiepin dissolved in 10 ml of anhydrous tetrahydrofuran. Thereafter, the mixture was reacted under cooling for 0.5 hr. at the room temperature and further under reflux condition for 3.5 hrs. After cooling, to the mixture was added water with stirring under cooling to decompose an excess of lithium aluminum hydroxide and the resulting mixture was filtered with the use of celite. The filtrate was extracted with chloroform, chloroform layer was washed with water and dried over anhydrous sodium sulfate. The solvent was evaporated to obtain 372 ml of an oily substance, which was chromatographed on a silica gel, eluted with n-hexane, and there was obtained 65 mg of 2-trifluoromethyl-9-chloro-10,11-dihydrodibenzo[b,f]thiepin.

Workup

  1. additionwas added
  2. customThereafter, the mixture was reacted
  3. temperatureunder cooling for 0.5 hr
  4. temperatureAfter cooling, to the mixture
  5. stirringwith stirring
  6. temperatureunder cooling
  7. filtrationthe resulting mixture was filtered with the use of celite
  8. extractionThe filtrate was extracted with chloroform, chloroform layer
  9. washwas washed with water
  10. dry with materialdried over anhydrous sodium sulfate
  11. customThe solvent was evaporated
  12. customto obtain 372 ml of an oily substance, which
  13. customwas chromatographed on a silica gel
  14. washeluted with n-hexane

Sources & evidence

ORD record
ord-05eb892f506c4273889af9c4480090a9
Source dataset
uspto-grants-1979_08
Patent number
US04166127

Reaction notes

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