Sodium Carbonate → 5-Bromo-4'-(ethylsulfonyl)-2'-methoxy-[1,1'-biphenyl]-2-ol

HRID 1846054노트

반응식

HRID 1846054 반응식
[CH2:1]([S:3]([C:6]1[CH:11]=[CH:10][C:9](B2OC(C)(C)C(C)(C)O2)=[C:8]([O:21][CH3:22])[CH:7]=1)(=[O:5])=[O:4])[CH3:2].[Br:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[C:26](I)[CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:23][C:24]1[CH:29]=[C:28]([C:9]2[CH:10]=[CH:11][C:6]([S:3]([CH2:1][CH3:2])(=[O:4])=[O:5])=[CH:7][C:8]=2[O:21][CH3:22])[C:27]([OH:30])=[CH:26][CH:25]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 109245324-Bromo-2-iodophenolHCID 867232082-(4-(Ethylsulfonyl)-2-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

생성물 1

HCID 867232765-Bromo-4'-(ethylsulfonyl)-2'-methoxy-[1,1'-biphenyl]-2-ol수율 44%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

To a stirred solution of 2-(4-(ethylsulfonyl)-2-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Preparation 21, 600 mg, 1.84 mmol) in dioxane (30 mL) and water (10 mL) were added 4-bromo-2-iodophenol (604 mg, 2.02 mmol), sodium carbonate (488 mg, 4.6 mmol) and tetrakis(triphenylphosphine)palladium(0) (106 mg, 0.092 mmol). The reaction was stirred at reflux for 18 hours. The reaction was allowed to cool temperature and then filtered through celite. The filtrate was reduced to dryness and then purified by silica gel column chromatography eluting with cyclohexane:EtOAc 1:1 followed by a second silica gel column chromatography eluting with CH2Cl2:MeOH 98:2 to give the title compound as pale yellow solid in 44% yield, 301 mg.

후처리

  1. temperatureat reflux for 18 hours
  2. temperatureto cool temperature
  3. filtrationfiltered through celite
  4. custompurified by silica gel column chromatography
  5. washeluting with cyclohexane:EtOAc 1:1
  6. washeluting with CH2Cl2:MeOH 98:2

출처 및 근거

ORD 기록
ord-05ed0762a00242b48bf17e1223ede3ed
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952008B2

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