Iodine → 3-Bromo-6-chlorophenanthrene

HRID 2117979ノート

反応式

HRID 2117979 の反応式
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

参加物

7

反応物 4

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

生成物 1

HCID 445415223-Bromo-6-chlorophenanthrene収率 100.9%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8078Cyclohexane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-31301e1f584e43b39d7b3979d534bc27
出典データセット
uspto-grants-2008_10
特許番号
US07442716B2

反応ノート

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