Cesium fluoride → HCID 66718378, compound

HRID 2404330Notes

Reaction equation

HRID 2404330 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:12]([F:15])([F:14])[F:13].[CH2:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1B(O)O)[CH3:17].[F-].[Cs+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>O1CCOCC1.O.CC(OC)(C)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:12]([F:15])([F:14])[F:13])[CH3:17]

Participants

9

Reactant 4

HCID 25953Cesium fluorideHCID 41008622-Ethylphenylboronic Acid (contains varying amounts of Anhydride)HCID 10891333Methyl 4-bromo-3-(trifluoromethyl)benzoateHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

Product 1

HCID 66718378HCID 66718378, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of methyl 4-bromo-3-(trifluoromethyl)benzoate (3.0 g, 10.6 mmol), 2-ethylphenylboronic acid (2.38 g, 15.9 mmol), cesium fluoride (4.83 g, 31.8 mmol), palladium acetate (48 mg, 0.21 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (261 mg, 0.64 mmol) was prepared in dioxane (30 mL) and water (15 mL), and then heated at 90° C. for 2.5 hours. The reaction mixture was diluted with MTBE (150 mL) and washed with water (50 mL) and brine (50 mL). The aqueous layers were extracted with MTBE (75 mL). The organic layers were combined, dried (MgSO4) and concentrated under vacuum. After purification by flash chromatography (silica, heptane/EtOAc), the title compound was obtained as a colorless oil (3.05 g, 93%). HPLC (Method A) Rt 5.6 min (Purity: 97.3%).

Workup

  1. washwashed with water (50 mL) and brine (50 mL)
  2. extractionThe aqueous layers were extracted with MTBE (75 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under vacuum
  5. customAfter purification by flash chromatography (silica, heptane/EtOAc)

Sources & evidence

ORD record
ord-e94efb440183407385c95b0759e5004e
Source dataset
uspto-grants-2014_08
Patent number
US08802704B2

Reaction notes

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