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

HRID 1174980Notes

Reaction equation

HRID 1174980 reaction equation
[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

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-abc9fbb11a9b4093b429a7219642b715
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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