Hydrochloric Acid → 5-Bromo-[1,1'-biphenyl]-2-carboxylic acid
Reaktionsgleichung
Br[C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Li+].[OH-].Cl>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CN1C(=O)CCC1.O>[Br:11][C:9]1[CH:10]=[C:2]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:3]([C:4]([OH:6])=[O:5])=[CH:7][CH:8]=1Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 70 °C
Versuchsvorschrift
A solution of 2,4-dibromo-benzoic acid, (2.3 g, 18.8 mmol), phenyl boronic acid (5 g, 17.9 mmol), Pd2(dba)3 (818 mg, 8.9 mmol) and LiOH (1.65 g, 39.3 mmol) in a 1:1 mixture of NMP/water (100 mL) was heated to 70° C. for 2 d. After this time, the reaction mixture was cooled to RT, and the reaction mixture was adjusted to pH=4-5 with 3 N HCl. The mixture was then extracted with ethyl acetate and the combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo and purified by normal phase silica gel column (EtOAc/PE 10:1 to 1:1) to afford 5-bromo-[1,1′-biphenyl]-2-carboxylic acid as a colorless oil.
Aufarbeitung
- temperatureAfter this time, the reaction mixture was cooled to RT
- extractionThe mixture was then extracted with ethyl acetate
- washthe combined organic layers were washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- custompurified by normal phase silica gel column (EtOAc/PE 10:1 to 1:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-20381d8e3b20480f9535fbeed6a5cd8c
- Quelldatensatz
- uspto-grants-2015_12
- Patentnummer
- US09199994B2
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