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

HRID 1373245Notes

Reaction equation

HRID 1373245 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[CH:7]([C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1)=[O:8].C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>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.O.C(O)C>[S:3]1[CH:4]=[CH:5][N:6]=[C:2]1[C:12]1[CH:13]=[CH:14][C:9]([CH:7]=[O:8])=[CH:10][CH:11]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 764302-BromothiazoleHCID 5910734-Formylphenylboronic Acid

Product 1

HCID 105356554-(1,3-Thiazol-2-yl)benzaldehydeYield 74%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of 2-bromothiazole (0.9 ml, 10 mmols), 4-formylphenylboronic acid (1.65 g, 11 mmols), sodium carbonate (2.65 g, 25 mmols), toluene (150 ml), ethanol (30 ml) and water (30 ml) was stirred in an argon atmosphere at room temperature for 30 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.58 mg, 0.5 mmols) was added thereto and heated under reflux for 15 hours. The reaction-mixture was cooled, poured into water, and extracted with ethyl acetate. The extract was washed with water and brine, then dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified through silica gel column chromatography, and then recrystallized from ethyl acetate/hexane to give 4-(2-thiazolyl)benzaldehyde (1.4 g, 74%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 15 hours
  3. temperatureThe reaction-mixture was cooled
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water and brine
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified through silica gel column chromatography
  9. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-ef48c5569fe34d44a0c37339c9b253a1
Source dataset
uspto-grants-2007_01
Patent number
US07160887B1

Reaction notes

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