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

HRID 2118003노트

반응식

HRID 2118003 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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 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.

후처리

  1. customquenched with water
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic layer 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)

출처 및 근거

ORD 기록
ord-5f3b759073fc4667b8260dfaef4fe9a0
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07442716B2

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