Potassium Hydroxide → 8-Bromo-2,3,4,5-tetrahydro-1-benzothiepine

HRID 373553Notes

Reaction equation

HRID 373553 reaction equation
[Br:1][C:2]1[CH:13]=[CH:12][C:5]2[C:6](=O)[CH2:7][CH2:8][CH2:9][S:10][C:4]=2[CH:3]=1.O.NN.[OH-].[K+]>C(O)COCCO>[Br:1][C:2]1[CH:13]=[CH:12][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][S:10][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 223374568-bromo-3,4-dihydro-2H-benzo[b]thiepin-5-one

Product 1

HCID 199354048-Bromo-2,3,4,5-tetrahydro-1-benzothiepineYield 72.5%

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Procedure

15.6 g of 8-bromo-3,4-dihydro-1-benzothiepin-5(2H)-one were dissolved in 70 ml of diethylene glycol. The solution was treated with 6.55 ml of hydrazine hydrate and 7.5 g of solid potassium hydroxide and heated to 180°-190° C. under reflux for about 30 hours. After cooling, the mixture was poured on to ice and extracted with ether. The organic phase was washed with water, dried and evaporated. Chromatography on silica gel with petroleum ether yielded 10.7 g of 8-bromo-2,3,4,5-tetrahydro-1-benzothiepine as a colorless oil.

Workup

  1. temperatureheated to 180°-190° C.
  2. temperatureunder reflux for about 30 hours
  3. temperatureAfter cooling
  4. additionthe mixture was poured on to ice
  5. extractionextracted with ether
  6. washThe organic phase was washed with water
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-b0f0703c78ac43d8b3aba03979754c12
Source dataset
uspto-grants-1992_11
Patent number
US05164387

Reaction notes

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