Hydrochloric Acid → 4-Bromo-2-(4-hydroxy-phenyl)-benzofuran-5-ol

HRID 1794544노트

반응식

HRID 1794544 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:11]=3[CH:12]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].C1C(=O)N([Br:31])C(=O)C1.Cl>CC#N>[Br:31][C:13]1[C:11]2[CH:12]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=3)[O:9][C:10]=2[CH:16]=[CH:15][C:14]=1[OH:17]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 6569362-(4-Hydroxy-phenyl)benzofuran-5-OL2회

생성물 1

HCID 222215874-Bromo-2-(4-hydroxy-phenyl)-benzofuran-5-ol

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

A solution of 75 2-(4-Hydroxy-phenyl)-benzofuran-5-ol (0.65 g, 2.9 mmol) in CH3CN (40 mL) was treated with K2CO3 (1 g, 7.1 mmol) followed by portionwise addition of NBS (0.36 g, 2.0 mmol). After stirring for approximately 30 minutes, the reaction was worked up by addition of 2 N HCl followed by 10% Na2SO3aq. and then the CH3CN was stripped off. The aqueous layer was extracted with EtOAc and washed with brine and dried over MgSO4. The reaction mixture was concentrated and chromatographed on silica gel (EtOAc/hexanes; 1:4): Mp 196–198° C.; 1H NMR (DMSO-d6) δ 9.93 (br s, 2 H), 7.76 (d, 2 H, J=8.5 Hz), 7.40 (d, 1 H, J=8.7 Hz), 7.04 (s, 1 H), 6.87 (dd, 2 H, J=9.0 Hz, 3.1 Hz); MS 305/307 (M+H)+.

후처리

  1. extractionThe aqueous layer was extracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationThe reaction mixture was concentrated
  5. customchromatographed on silica gel (EtOAc/hexanes; 1:4)

출처 및 근거

ORD 기록
ord-ae62df5144ff42c992ece7772194ba0d
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07022733B2

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