Cesium fluoride → HCID 67267092, compound

HRID 598087Notes

Reaction equation

HRID 598087 reaction equation
Cl[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:15][C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=1B(O)O.[F-].[Cs+]>COCCOC.C(OCC)(=O)C.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>[CH3:15][C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=1[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

7

Reactant 3

HCID 25953Cesium fluorideHCID 603613Benzoic acid, 2-chloro-6-nitro-, methyl esterHCID 4198739(2,4-Dimethylphenyl)boronic acid

Product 1

HCID 67267092HCID 67267092, compoundYield 47.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture containing 0.5 g (2.3 mmol) of methyl 2-chloro-6-nitrobenzoate, 0.76 g (3.5 mmol) of 2,4-dimethylphenyl boronic acid, 0.7 g (4.6 mmol) of cesium fluoride, and 0.27 g (0.23 mmol) of tetrakis(triphenylphosphine)palladium(0) in 10 ml of 1,2-dimethoxyethane was heated to 100° C. under a nitrogen atmosphere overnight. The reaction was cooled to room temperature, diluted with ethyl acetate and washed with saturated sodium bicarbonate. The organic phase was dried over magnesium sulfate. Filtration, removal of solvent and purification of the residue via biotage eluting with 20% ethyl acetate/hexanes gave 0.312 g (47%) of product.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. washwashed with saturated sodium bicarbonate
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationFiltration, removal of solvent and purification of the residue via biotage
  5. washeluting with 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-c8a076457b1b41068c6c8a4f92149b1a
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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