Dimethylformamide → 4'-Hydroxy-2'-methyl-biphenyl-4-carboxylic Acid Methyl Ester
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].[C:10](=[O:13])([O-])[O-].[Cs+].[Cs+].CN([CH:19]=[O:20])C>O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:10][O:13][C:19]([C:2]1[CH:7]=[CH:6][C:5]([C:2]2[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=2[CH3:9])=[CH:4][CH:3]=1)=[O:20]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 75 °C
Procedure
To a solution of 4-bromo-3-methyl phenol (0.300 g, 1 equiv) in DMF (5 mL) are added 4-methylester phenyl boronic acid (0.58 g, 2 equiv), dppf (0.27 g, 0.3 equiv), palladium acetate (0.036 g, 0.1 equiv), and cesium carbonate (1.04 g, 2 equiv). The reaction mixture is heated to 75° C. for 1 h. The reaction is cooled to room temperature and is diluted with water. The resulting solution is extracted with ethyl acetate. The combined organic layers are combined and washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue is purified via flash chromatography eluting with 3% ethyl acetate in toluene to give the desired product (0.224 g, 58%). ES/MS m/e 241.3 (M−1).
Workup
- temperatureThe reaction is cooled to room temperature
- extractionThe resulting solution is extracted with ethyl acetate
- washwashed with brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe crude residue is purified via flash chromatography
- washeluting with 3% ethyl acetate in toluene
Sources & evidence
- ORD record
- ord-a0613380d0cc4bdf8c5740110e10a8db
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08106077B2
Reaction notes
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