4-Iodotoluene → HCID 86691023, compound

HRID 1191954Notes

Reaction equation

HRID 1191954 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=1.[CH3:17][C:18]1[CH:23]=[CH:22][C:21](I)=[CH:20][CH:19]=1>C(=O)([O-])[O-].[Ag+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:18]1([CH3:17])[CH:23]=[CH:22][C:21]([C:5]2[S:1][C:2]([C:6]3[CH:7]=[CH:8][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:15][CH:16]=3)=[N:3][CH:4]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 122074-IodotolueneHCID 23510389HCID 23510389, compound

Product 1

HCID 86691023HCID 86691023, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 178418647HCID 178418647, compoundCatalyst

Conditions

Temperature
60 °C

Procedure

In a sealed tub was added ethyl 4-(thiazol-2-yl)benzoate (100 mg, 0.43 mmol), 4-methyliodobenzene (111 mg, 0.51 mmol), silver carbonate (236 mg, 0.86 mmol) and tetrakis(triphenylphosphine)palladium (0) (11.2 mg, 0.86 mmol). The flask was purged with nitrogen three times and then was added acetonitrile (1.8 mL). The mixture was stirred under Ar atmosphere for 12 h at 60° C. When the reaction completed, the inorganic solids were filtered on (Celite®) and the residue was washed several times with dichloromethane, then filtered and evaporated. Flash chromatography of the residue on silica gel (SiO2, hexane:ethyl acetate, 9:1) afforded 115.8 mg of ethyl 4-(5-(p-tolyl)thiazol-2-yl)benzoate as a white crystalline solid (84% yield). EM (IE): m/z (%): 323.1; (M+, 100). HRMS (ESI): calculated for C19H18NO2S: 324.1053. found: 324.1055.

Workup

  1. customThe flask was purged with nitrogen three times
  2. additionwas added acetonitrile (1.8 mL)
  3. filtrationthe inorganic solids were filtered on (Celite®)
  4. washthe residue was washed several times with dichloromethane
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-92c9a653a66f4b7a87e2d7f450454bf3
Source dataset
uspto-grants-2014_03
Patent number
US08680126B2

Reaction notes

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