Acetic Acid → 9-(3-bromopropylidene)-9H-thioxanthene

HRID 863554Notes

Reaction equation

HRID 863554 reaction equation
[CH:1]1([C:4]2(O)[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[S:11][C:10]3[C:5]2=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:3][CH2:2]1.C(O)(=O)C.[BrH:23]>O>[Br:23][CH2:3][CH2:2][CH:1]=[C:4]1[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[S:11][C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2

Participants

5

Reactant 3

HCID 176Acetic Acid2×HCID 260Hydrogen BromideHCID 187993359-cyclopropyl-9H-thioxanthen-9-ol

Product 1

HCID 233013389-(3-bromopropylidene)-9H-thioxanthene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the above crude alcohol (25.2 g) was added glacial acetic acid (120 ml). The mixture was cooled on an ice-bath and a mixture of glacial acetic acid (60 ml) and 47% hydrobromic acid (30 ml) was added. The mixture was stirred for 30 minutes, poured into water (600 ml) and extracted with diethyl ether (3×200 ml). The combined organic phases were washed with water, dried (Na2SO4) and the solvent was evaporated in vacuo to give 19.5 g of crude 9-(3-bromo-1-propylidene)-9H-thioxanthene. Rf =0.35 (SiO2 ; THF/heptane=1:9).

Workup

  1. temperatureThe mixture was cooled on an ice-bath
  2. additionwas added
  3. extractionextracted with diethyl ether (3×200 ml)
  4. washThe combined organic phases were washed with water
  5. dry with materialdried (Na2SO4)
  6. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-44ef8ea0ebb844238aa5a34d7e9c4543
Source dataset
uspto-grants-1998_02
Patent number
US05721254

Reaction notes

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