2-Bromothiazole → 2-(1,3-Thiazol-2-yl)benzaldehyde

HRID 1827278Notes

Reaction equation

HRID 1827278 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1B(O)O)=[O:8].C([O-])(O)=O.[Na+]>COCCOC.O.[Pd].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.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>[S:3]1[CH:4]=[CH:5][N:6]=[C:2]1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH:7]=[O:8]

Participants

7

Reactant 3

HCID 764302-BromothiazoleHCID 2921892-Formylphenylboronic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 155324822-(1,3-Thiazol-2-yl)benzaldehyde

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a mixture of 2-bromothiazole (826 mg, 4.99 mmol) and tetrakis(triphenylphosphine) palladium (0) (175 mg, 0.151 mmol) in 1,2-dimethoxyethane (20 mL) was added 2-formylbenzeneboronic acid (0.9017 g, 6.01 mmol) and 1N aqueous NaHCO3 (8 mL). The resultant mixture was heated at reflux for 6 hrs. The reaction mixture was diluted with water and extracted with EtOAc (2×50 mL). The organic solution was dried over Na2SO4, filtered and concentrated. The crude product was purified by gradient flash chromatography (10% to 25% EtOAc in hexane) to yield 2-(2-thiazolyl)benzaldehyde as a white solid.

Workup

  1. temperatureat reflux for 6 hrs
  2. extractionextracted with EtOAc (2×50 mL)
  3. dry with materialThe organic solution was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by gradient flash chromatography (10% to 25% EtOAc in hexane)

Sources & evidence

ORD record
ord-5d623c59fae242bcac1f00568476b5a4
Source dataset
uspto-grants-2006_05
Patent number
US07053101B2

Reaction notes

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