Cesium fluoride → HCID 57413377, compound

HRID 1948664Notes

Reaction equation

HRID 1948664 reaction equation
F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.[F-].[Cs+].[CH3:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:23]=1B(O)O.Br[C:33]1[C:34]([CH3:43])=[C:35]([CH:40]=[CH:41][CH:42]=1)[C:36]([O:38][CH3:39])=[O:37]>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]>[CH3:43][C:34]1[C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:40][CH:41]=[CH:42][C:33]=1[C:23]1[C:24]([CH3:28])=[CH:25][CH:26]=[CH:27][C:22]=1[CH3:21]

Participants

6

Reactant 4

HCID 25953Cesium fluorideHCID 5833222,6-Dimethylphenylboronic acidHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 12929135Methyl 3-Bromo-2-methylbenzoate

Product 1

HCID 57413377HCID 57413377, compound

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
70 °C

Procedure

To a two-neck round bottom flask with a magnetic stirring bar, was added tris(dibenzylideneacetone)dipalladium(0) (120 mg, 0.131 mmol), tri-t-butylphosphonium tetrafluoroborate (76 mg, 0.262 mmol), cesium fluoride (2.65 g, 17.5 mmol), 2,6-dimethylphenylboronic acid (1.3 g, 8.73 mmol), and the compound from Step A (1 g, 4.4 mmol). One neck of the flask was connected to a vacuum line while another neck was fitted with a argon balloon. The flask was then purged 8-10 times with argon. The vacuum line was replaced with a septum and anhydrous THF (10 mL) was added by syringe. The mixture was stirred in a 70° C. oil bath for 16 h. The reaction solution was filtrated and concentrated. The residue was purified by column chromatography on silica gel Biotage 40S™, eluting with EtOAc/hexane (10:1) to give the title compound as a clear oil.

Workup

  1. customOne neck of the flask was connected to a vacuum line while another neck
  2. customwas fitted with a argon balloon
  3. customThe flask was then purged 8-10 times with argon
  4. additionwas added by syringe
  5. filtrationThe reaction solution was filtrated
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel Biotage 40S™
  8. washeluting with EtOAc/hexane (10:1)

Sources & evidence

ORD record
ord-62c557948f0b405e960c343e8127cce4
Source dataset
uspto-grants-2013_03
Patent number
US08399507B2

Reaction notes

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