Potassium Carbonate → 2',4'-Dichloro-biphenyl-4-carboxylic acid

HRID 1174980ノート

反応式

HRID 1174980 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1B(O)O.C[O:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][C:18](I)=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>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>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:18]1[CH:19]=[CH:20][C:15]([C:14]([OH:22])=[O:13])=[CH:16][CH:17]=1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 69273Methyl 4-iodobenzoateHCID 2734659(2,4-Dichlorophenyl)boronic acid

生成物 1

HCID 107542792',4'-Dichloro-biphenyl-4-carboxylic acid収率 54.5%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒2 回HCID 312751,4-Dioxane溶媒

実験手順

A solution of 2,4-dichlorophenyl boronic acid (3.96 g, 15.11 mmol) and 4-Iodo-benzoic acid methyl ester (2.88 g, 15.11 mmol), K2CO3 (7.31 g, 52.89 mmol) in 1,4-dioxane (85 mL), and water (20 mL) is purged with nitrogen for 10 min. Pd(PPh3)4 (0.87 g, 0.756 mmol) is added and the resulting reaction mixture is refluxed overnight. The reaction is diluted with water and extracted with Et2O. The combined organic layers are washed with water, dried with MgSO4, and concentrated. The crude material is purified by chromatography to give the title compound (2.20 g, 50%). LC/MS (m/z): calcd for C13H18Cl2O2: 267.1; found: 266.9.

後処理

  1. customthe resulting reaction mixture
  2. temperatureis refluxed overnight
  3. extractionextracted with Et2O
  4. washThe combined organic layers are washed with water
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated
  7. customThe crude material is purified by chromatography

出典と根拠

ORDレコード
ord-abc9fbb11a9b4093b429a7219642b715
出典データセット
uspto-grants-2010_11
特許番号
US07838543B2

反応ノート

読み込み中…