4-Bromobenzaldehyde → 4-(1,3-Thiazol-2-yl)benzaldehyde

HRID 488900Notes

Reaction equation

HRID 488900 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:15]1[S:16][CH:17]=[CH:18][N:19]=1)CCC>CC#N.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd](Cl)Cl>[S:16]1[CH:17]=[CH:18][N:19]=[C:15]1[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 707414-BromobenzaldehydeHCID 27632592-(Tributylstannyl)-1,3-thiazole

Product 1

HCID 105356554-(1,3-Thiazol-2-yl)benzaldehydeYield 79.2%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 0.500 g (2.70 mmol) of 4-bromobenzaldehyde and 1.00 g (2.67 mmol) of 2-tributylstannylthiazole in MeCN (25 mL), degassed by bubbling N2 through for 10 min, was added 0.100 g (0.140 mmol) of palladium dichloride bis(triphenylphosphine). The mixture was heated to 60° C. for 15 h. The mixture was cooled to room temperature and filtered through diatomaceous earth. The mixture was diluted with H2O and washed with EtOAc. The combined organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by flash silica gel chromatography to provide 0.400 g (79.1%) of 4-thiazol-2-yl-benzaldehyde as a yellow solid.

Workup

  1. customby bubbling N2 through for 10 min
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered through diatomaceous earth
  4. additionThe mixture was diluted with H2O
  5. washwashed with EtOAc
  6. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-7d47ed4879164c7b87c55f8509480aad
Source dataset
uspto-grants-2005_12
Patent number
US06974870B2

Reaction notes

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