Iodine → HCID 15158873, compound

HRID 359621Notes

Reaction equation

HRID 359621 reaction equation
II.BrCCBr.[Mg].Br[C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH3:16])[CH:10]=1.[C:17]1(=O)[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH2:18]1.[Cl-].[NH4+]>C(O)(=O)C.O1CCCC1>[CH3:16][C:11]1[CH:10]=[C:9]([C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19][CH:18]=2)[CH:14]=[C:13]([CH3:15])[CH:12]=1

Participants

9

Reactant 6

HCID 807Iodine2×HCID 67351-IndanoneHCID 78391,2-DibromoethaneHCID 25517Ammonium ChlorideHCID 136357Benzene, 1-bromo-3,5-dimethyl-HCID 5462224Magnesium

Product 1

HCID 15158873HCID 15158873, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

20 mg. of iodine and 0.2-0.3 ml. of 1,2-dibromoethane are added to a suspension of 5 g. (0.21 mole) of magnesium in 15 ml. of dry tetrahydrofuran stirred at 20°-25° C. under nitrogen. When the reaction commences and the color of iodine disappears, a solution of 38 g. (0.205 mole) of 1-bromo-3,5-dimethylbenzene in 150 ml. of dry tetrahydrofuran is added dropwise over a period of about 1 hour at a rate such that the reaction mixture gently refluxes, the reaction mixture is refluxed for 1 hour and cooled to 20°-25° C., a solution of 26 g. (0.197 mole) of 1-indanone in 150 ml. of dry tetrahydrofuran is added dropwise over a period of 30 minutes, and the reaction mixture is maintained at 20°-25° C. for 30 minutes, the reaction mixture being stirred under nitrogen throughout. The reaction mixture is poured into cold (0°- 5° C.) saturated ammonium chloride solution, and the mixture is extracted three times with ethyl acetate. The ethyl acetate extracts are combined, washed with water, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered and evaporated at reduced pressure to obtain a yellow oil (54 g.). The obtained oil is dissolved in 70 ml. of glacial acetic acid, and the reaction mixture is refluxed for 30 minutes and evaporated at reduced pressure to obtain a brown oil. The oil is subjected to a Kugelrohr distillation to obtain the product as a yellow oil (34 g. (79%)) (collected at a bath temperature of 115°-125° C. at 1 mm. Hg.).

Workup

  1. customWhen the reaction commences
  2. temperaturethe reaction mixture is refluxed for 1 hour
  3. temperaturecooled to 20°-25° C.
  4. temperaturethe reaction mixture is maintained at 20°-25° C. for 30 minutes
  5. extractionthe mixture is extracted three times with ethyl acetate
  6. washwashed with water
  7. washwashed with saturated sodium chloride solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customevaporated at reduced pressure
  11. customto obtain a yellow oil (54 g.)
  12. dissolutionThe obtained oil is dissolved in 70 ml
  13. customevaporated at reduced pressure
  14. customto obtain a brown oil
  15. distillationThe oil is subjected to a Kugelrohr distillation

Sources & evidence

ORD record
ord-5bbdaf403b1845ba8a64da533d9820f8
Source dataset
uspto-grants-1991_03
Patent number
US05001255

Reaction notes

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