Chloroform → HCID 59300121, compound

HRID 2236463

Reaction equation

HRID 2236463 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7](I)=[C:6]([O:11][CH3:12])[CH:5]=1.C(Cl)(Cl)Cl.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.[CH2:31]([Zn]Br)[CH2:32][CH2:33][CH3:34]>CN(C)C=O.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].O.CCOCC>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([CH2:31][CH2:32][CH2:33][CH3:34])=[C:6]([O:11][CH3:12])[CH:5]=1

Participants

9

Reactant 4

HCID 6212ChloroformHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 11243290Methyl 4-iodo-3-methoxybenzoateHCID 178448257HCID 178448257, compound

Product 1

HCID 59300121HCID 59300121, compound

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

4-Iodo-3-methoxy-benzoic acid methyl ester (292 mg, 1 mmol) and Pd2(dba)3.CHCl3 (25 mg, 0.025 mmol) and P(tBu)3 (0.25 mL, 10% in hexane, 0.08 mmol) and n-BuZnBr (4 mL, 0.5 M in THF, 2.0 mmol) is mixed in N,N-dimethylformamide (4 mL) together and degassed. After stirring at room temperature for 1 hour, analysis of TLC suggested no starting material left and reaction is stopped. Et2O and H2O were then added and the ether layer is washed with water and dried. After the removal of ether, the residue is directly used in the next step after pass through a short column.

Workup

  1. customdegassed
  2. waitleft
  3. customreaction
  4. washthe ether layer is washed with water
  5. customdried
  6. customAfter the removal of ether

Sources & evidence

ORD record
ord-234feb9bdb2e403eb3608fe74aab6c61
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Linked notes

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