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

HRID 1846054ノート

反応式

HRID 1846054 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-05ed0762a00242b48bf17e1223ede3ed
出典データセット
uspto-grants-2015_02
特許番号
US08952008B2

反応ノート

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