3,3,3-Trifluoropropene → HCID 57804190, compound

HRID 2102896Notes

Reaction equation

HRID 2102896 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[CH:3]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C([O-])(=O)C.[K+].[F:39][C:40]([F:44])([F:43])[CH:41]=[CH2:42].CN(C)C(=O)C>CCCC[N+](CCCC)(CCCC)CCCC.[Cl-].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:11][C:4]1[CH:3]=[C:2](/[CH:42]=[CH:41]/[C:40]([F:44])([F:43])[F:39])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Participants

8

Reactant 5

HCID 126723,3,3-TrifluoropropeneHCID 31374DimethylacetamideHCID 80271Tri-o-tolylphosphineHCID 995704-Bromo-2-methylbenzoic acidHCID 517044Potassium Acetate

Product 1

HCID 57804190HCID 57804190, compound

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
180 °C

Procedure

A mixture of 4-bromo-2-methylbenzoic acid (25 g, 0.12 mol), tri-o-tolylphosphine (7.1 g, 0.023 mol), tetra-N-butylammonium chloride (9.7 g, 0.035 mol), potassium acetate (22.8 g, 0.232 mol), 3,3,3-trifluoroprop-1-ene (89 g, 0.93 mol), palladium acetate (1.3 g, 0.0058 mol) and N,N-dimethylacetamide (150 mL, 1.6 mol) was sealed in a Parr instrument and stirred at 180° C. for 120 h. After cooling, the reaction mixture was filtered through Celite® and the filtrate was partitioned between EtOAc and 1N HCl (pH 2-3). The organic layer was separated and washed with brine, dried (Na2SO4) and concentrated under vacuum. The residue was purified by column chromatography on silica gel to give a crude product (which contained a small amount of the correspnding (Z)-isomer).

Workup

  1. customwas sealed in a Parr instrument
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtered through Celite®
  4. customthe filtrate was partitioned between EtOAc and 1N HCl (pH 2-3)
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated under vacuum
  9. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-259a0d58441649bb8b9b86bfc17aee8a
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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