HCID 10544300, compound → HCID 10853776, compound

HRID 1483184Notes

Reaction equation

HRID 1483184 reaction equation
[C:1]1([C:7]#[C:8][C:9]([O:11][C:12]2[CH:17]=[C:16]([CH3:18])[C:15]([Br:19])=[C:14]([CH3:20])[CH:13]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>ClCCl.FC(F)(F)C(O)=O.ClCCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:19][C:15]1[C:16]([CH3:18])=[C:17]2[C:12](=[CH:13][C:14]=1[CH3:20])[O:11][C:9](=[O:10])[CH:8]=[C:7]2[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 1

HCID 10544300HCID 10544300, compound

Product 1

HCID 10853776HCID 10853776, compoundYield 77%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a stirring solution of 4-bromo-3,5-dimethyl-phenyl 3-phenylpropiolate (1-1) (9839 mg, 30.00 mmol) in dichloromethane (15 mL) and trifluoroacetic acid (45 mL) was added palladium acetate (350 mg, 1.60 mmol) under ice-cooling. After stirred for 2 h under ice-cooling, the mixture was diluted with 1,2-dichloroethane and evaporated to dryness. The residue was chromatographed on a silica gel (chloroform:hexanes=1:1-3:2) to give the title compound 1-2 (7581 mg, 77% yield) as a dark yellow solid.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. customevaporated to dryness
  4. customThe residue was chromatographed on a silica gel (chloroform:hexanes=1:1-3:2)

Sources & evidence

ORD record
ord-715617b53f07400f842ad91a0996f8d2
Source dataset
uspto-grants-2016_08
Patent number
US09416121B2

Reaction notes

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