Cesium carbonate → HCID 86708720, compound

HRID 1751383Notes

Reaction equation

HRID 1751383 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[C:4]([CH:11]=O)[CH:3]=1.Br[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[CH2:21][C:22]#[N:23].C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.CO.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[C:14]3[C:15](=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=3)[C:21]([C:22]#[N:23])=[CH:11][C:4]=2[CH:3]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 237304254-Chloro-2-formylphenylboronic Acid (contains varying amounts of Anhydride)HCID 696738372-(2-Bromo-5-chlorophenyl)acetonitrile

Product 1

HCID 86708720HCID 86708720, compoundYield 20.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a microwave vial was added 4-chloro-2-formylphenylboronic acid (480 mg, 2.6 mmol), 2-(2-bromo-5-chlorophenyl)acetonitrile (500 mg, 2 mmol), tetrakis(triphenyl phosphine)palladium (0) (100 mg, 0.085 mmol) and cesium carbonate (2.12 g, 6.5 mmol) sequentially. The mixture was suspended in toluene (10 mL) and methanol (5 mL). Then the reaction vial was sealed and place in a microwave reactor and irradiated at 150° C. for 10 minutes. The reaction was cooled to room temperature, diluted with ethyl acetate, and filtered through a short celite pad. The solution was concentrated. The crude residue was purified by flash chromatography to yield 2,7-dichlorophenanthrene-9-carbonitrile (110 mg, 19%)

Workup

  1. customThen the reaction vial was sealed
  2. customplace in a microwave reactor and irradiated at 150° C. for 10 minutes
  3. filtrationfiltered through a short celite pad
  4. concentrationThe solution was concentrated
  5. customThe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-c180a580883245e3a276770e5b373492
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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