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Boron tribromide → HCID 53663674, 화합물

HRID 1824903
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HRID 1824903 반응식
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([C:13]1[CH:18]=[CH:17][C:16]([CH:19]=[CH:20][C:21]([OH:23])=[O:22])=[CH:15][CH:14]=1)[CH:8]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:7][CH2:6]2.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([C:13]1[CH:18]=[CH:17][C:16]([CH:19]=[CH:20][C:21]([OH:23])=[O:22])=[CH:15][CH:14]=1)[CH:8]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:7][CH2:6]2
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참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 54486062HCID 54486062, 화합물

생성물 1

HCID 53663674HCID 53663674, 화합물수율 39%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of ether 6e (120 mg, 0.312 mmol) in CH2Cl2 (12 mL) at 0° C. was added 1M boron tribromide in CH2Cl2 (4 mL). The mixture was stirred 1.5 h at room temperature and then quenched with ice/H2O. After stirring for 2 h, the mixture was extracted with CH2Cl2. The combined organic layers were washed with water and dried (MgSO4). The solvent was removed under reduced pressure and the residue chromatographed (silica gel, 10-20% methanol/CH2Cl2) to give phenol 6f as a white solid (45 mg, 39%): ESI m/z: 369 (M−H−, 100%).

후처리

  1. customquenched with ice/H2O
  2. stirringAfter stirring for 2 h
  3. extractionthe mixture was extracted with CH2Cl2
  4. washThe combined organic layers were washed with water
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed under reduced pressure
  7. customthe residue chromatographed (silica gel, 10-20% methanol/CH2Cl2)

출처 및 근거

ORD 기록
ord-03f0fb48af4c4beaa122966b0dbb1f1b
출처 데이터셋
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07045540B2

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