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

HRID 1174980노트

반응식

HRID 1174980 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

HCID 107542792',4'-Dichloro-biphenyl-4-carboxylic acid수율 54.5%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매2회HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-abc9fbb11a9b4093b429a7219642b715
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07838543B2

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