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Sodium Sulfite → 4-Chloro-2-(4-hydroxy-phenyl)-7-methoxy-benzofuran-5-ol

HRID 1794502
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HRID 1794502 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[C:16]([O:17][CH3:18])=[CH:15][C:14]([OH:19])=[CH:13][C:11]=3[CH:12]=2)=[CH:4][CH:3]=1.C1C(=O)N([Cl:27])C(=O)C1.[O-]S([O-])=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>CC#N.[Cl-].[Na+].O>[Cl:27][C:13]1[C:11]2[CH:12]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=3)[O:9][C:10]=2[C:16]([O:17][CH3:18])=[CH:15][C:14]=1[OH:19]
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참가 물질

7

반응물 4

HCID 24437Sodium SulfiteHCID 31398ChlorosuccinimideHCID 516892Sodium BicarbonateHCID 102860222-(4-Hydroxy-phenyl)-7-methoxy-benzofuran-5-ol

생성물 1

HCID 101930274-Chloro-2-(4-hydroxy-phenyl)-7-methoxy-benzofuran-5-ol수율 22.9%

시약·촉매·용매 2

HCID 6342
Acetonitrile
용매
HCID 57417360Sodium chloride; water용매

실험 절차

Compound 62 (0.1 g, 0.39 mmol) in CH3CN (10 mL) was treated with portionwise addition of NCS (0.033 g, 0.24 mmol). After addition, 10% Na2SO3 aq was added followed by NaHCO3 and brine. The EtOAc layer was dried over MgSO4, filtered, concentrated and chromatographed on silica gel (3:7 EtOAc/hexanes) to yield 0.016 g of the product: Mp=176–177° C.; 1H NMR (DMSO-d6) δ 9.89 (br s, 2 H), 7.74 (d, 2 H, J=8.6 Hz), 7.10 (s, 1 H), 6.87 (d, 2 H, J=8.7 Hz), 6.55 (s, 1 H), 3.91 (s, 3 H); MS 291 (M+H)+.

후처리

  1. additionwas added
  2. dry with materialThe EtOAc layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed on silica gel (3:7 EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-36c33e5da4404ce9a3aea2dcc5ef6122
출처 데이터셋
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07022733B2

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