Cesium carbonate → HCID 86697028, compound

HRID 536175Notes

Reaction equation

HRID 536175 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[C:5]([C:10]([F:13])([F:12])[F:11])[CH:4]=1.[B-](F)(F)(F)[C:15]1[CH:20]=[CH:19][C:18]([CH:21]=[O:22])=[CH:17][CH:16]=1.[K+].C([O-])([O-])=O.[Cs+].[Cs+]>COC1CCCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[Cl:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][C:15]2[CH:20]=[CH:19][C:18]([CH:21]=[O:22])=[CH:17][CH:16]=2)=[CH:4][C:5]=1[C:10]([F:13])([F:12])[F:11]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 27781144-Chloro-3-(trifluoromethyl)benzyl bromideHCID 23697319Potassium trifluoro(4-formylphenyl)borate(1-)

Product 1

HCID 86697028HCID 86697028, compoundYield 51.9%

Reagents, catalysts & solvents 3

HCID 178418807HCID 178418807, compoundCatalystHCID 962WaterSolventHCID 138539Cyclopentyl methyl etherSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 4-(bromomethyl)-1-chloro-2-(trifluoromethyl)benzene (4.5 g, 16.45 mmol), potassium trifluoro(4-formylphenyl)borate (3.52 g, 16.62 mmol), PdCl2(dppf)-CH2Cl2 adduct (0.672 g, 0.823 mmol) and Cs2CO3 (16.08 g, 49.4 mmol) in cyclopentyl methyl ether (100 mL) and water (100 mL). The mixture was charged with Argon and stirred for overnight at 80° C. The result mixture was cooled to room temperature and partitioned with water 100 mL and ethyl acetate 100 mL. The organic phase was washed by water, brine and dried over sodium sulfate, the solvent was removed and the residue was purified via flash column chromatography. Removed the solvent afforded the title compound (2.55 g). LC-MS (ESI): m/z 299 [M+H]+

Workup

  1. additionThe mixture was charged with Argon
  2. temperatureThe result mixture was cooled to room temperature
  3. custompartitioned with water 100 mL and ethyl acetate 100 mL
  4. washThe organic phase was washed by water, brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was removed
  7. customthe residue was purified via flash column chromatography
  8. customRemoved the solvent

Sources & evidence

ORD record
ord-881d5b2c67b74d76915324d994e800fa
Source dataset
uspto-grants-2014_10
Patent number
US08859573B2

Reaction notes

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