Cesium carbonate → HCID 58073894, compound

HRID 1470581Notes

Reaction equation

HRID 1470581 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([F:15])[CH:9]=1.[CH3:16][O:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1>C1(C)C=CC=CC=1.O>[F:15][C:10]1[CH:9]=[C:8]([C:22]2[CH:21]=[CH:20][CH:19]=[C:18]([O:17][CH3:16])[CH:23]=2)[CH:13]=[CH:12][C:11]=1[CH3:14]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 1710404-Bromo-2-fluorotolueneHCID 2734370(3-Methoxyphenyl)boronic acid

Product 1

HCID 58073894HCID 58073894, compoundYield 75.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

A mixture of toluene (22.7 mL) and water (22.7 mL+7.5 mL) was degassed with nitrogen for 30 min. A mixture of cesium carbonate (3.3 g, 1.04 mmol), 4-bromo-2-fluoro-1-methyl-benzene (1.0 g, 5.2 mmol), 3-methoxyphenylboronic acid (0.8 g, 5.2 mmol) and tetrakis triphenyl phosphene palladium (0.294 g, 0.26 mmol) was added to the above degassed aq. toluene and the resulting mixture was refluxed for 5 h. After the reaction was completed, it was cooled and extracted with ethyl acetate. The combined ethyl acetate layers were dried over sodium sulphate and concentrated. The residue was purified by column chromatography using 10% ethyl acetate in hexane to obtain the title compound (0.85 g, 74%).

Workup

  1. customwas degassed with nitrogen for 30 min
  2. temperaturethe resulting mixture was refluxed for 5 h
  3. temperatureit was cooled
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined ethyl acetate layers were dried over sodium sulphate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-0ef196a134e74eb49e96464f8ac13f71
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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