Iodine → 3-Bromo-6-chlorophenanthrene

HRID 549478Notes

Reaction equation

HRID 549478 reaction equation
O.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.C1OC1C.II>C1COCC1.C1CCCCC1>[Br:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:9]=[CH:10][C:11]3[C:12]([C:7]=2[CH:8]=1)=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=3

Participants

7

Reactant 4

HCID 807IodineHCID 962WaterHCID 6378Propylene OxideHCID 53911528HCID 53911528, compound

Product 1

HCID 445415223-Bromo-6-chlorophenanthreneYield 100.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8078CyclohexaneSolvent

Procedure

A 2 L vessel equipped with a pyrex inner water-cooled jacket was charged with 5.16 g (17 mmol) of 1-bromo-4-[2-(4-chlorophenyl)vinyl]benzene from Step 1, 2 L of cyclohexane, 25 mL of THF, 25 mL of propylene oxide and 6.7 g (26 mmol) of iodine. The stirring solution was degassed by bubbling nitrogen and was exposed to UV light for 24 hrs by inserting a 450 W medium pressure mercury lamp in the inner. The reaction was quenched with 10% Na2S2O3 and aqueous layer was extracted with ethyl acetate. Combined organic layers were washed with brine, dried over Na2SO4 and volatiles were removed under reduced pressure. The residue was swished in a minimal amount of ethyl acetate to afford approx. 5 g of 3-bromo-6-chlorophenanthrene as a solid.

Workup

  1. temperaturecooled jacket
  2. customThe stirring solution was degassed
  3. customby bubbling nitrogen
  4. customThe reaction was quenched with 10% Na2S2O3 and aqueous layer
  5. extractionwas extracted with ethyl acetate
  6. washCombined organic layers were washed with brine
  7. dry with materialdried over Na2SO4 and volatiles
  8. customwere removed under reduced pressure

Sources & evidence

ORD record
ord-196927f671854ec7a61f8b99155115da
Source dataset
uspto-grants-2011_05
Patent number
US07943649B2

Reaction notes

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