Iodine → 3-Bromo-6-chlorophenanthrene

HRID 2117979노트

반응식

HRID 2117979 반응식
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

참가 물질

7

반응물 4

HCID 807IodineHCID 962WaterHCID 6378Propylene OxideHCID 539115281-Bromo-4-(4-chlorostyryl)benzene

생성물 1

HCID 445415223-Bromo-6-chlorophenanthrene수율 100.9%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8078Cyclohexane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-31301e1f584e43b39d7b3979d534bc27
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07442716B2

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