Triphenylphosphine → 3-Bromo-6-(2-cyclopropylethoxy)phenanthrene

HRID 549504ノート

反応式

HRID 549504 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[CH:11][C:10]1[CH:9]=[CH:8][C:7]([OH:16])=[CH:6][C:5]2=1.[CH:17]1([CH2:20][CH2:21]O)[CH2:19][CH2:18]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)(C)C)=O)=O)(C)C>C1COCC1>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[CH:12]=[CH:11][C:10]3[C:5]([C:4]=2[CH:3]=1)=[CH:6][C:7]([O:16][CH2:21][CH2:20][CH:17]1[CH2:19][CH2:18]1)=[CH:8][CH:9]=3

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 1376422-Cyclopropylethan-1-olHCID 6034084Di-tert-butyl diazene-1,2-dicarboxylateHCID 86614876HCID 86614876、化合物

生成物 1

HCID 866148853-Bromo-6-(2-cyclopropylethoxy)phenanthrene

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture of 6-bromophenanthren-3-ol (3 g, 11 mmol) from Step 1 of Route A of Example 168, 2-cyclopropylethanol (2.85 g, 33 mmol) and triphenylphosphine (5.78 g, 22 mmol) in THF (50 mL) was added di-tert-butylazodicarboxylate (5.08 g, 22 mmol). The reaction mixture was stirred at room temperature overnight, then quenched with water. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The material was purified by flash chromatography on silica (100% hexanes) to afford 3-bromo-6-(2-cyclopropylethoxy)phenanthrene.

後処理

  1. customquenched with water
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe material was purified by flash chromatography on silica (100% hexanes)

出典と根拠

ORDレコード
ord-712bfce505424360bb8e65e2a7510f71
出典データセット
uspto-grants-2011_05
特許番号
US07943649B2

反応ノート

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