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

HRID 2416502Notes

Reaction equation

HRID 2416502 reaction equation
C([O-])(O)=O.[Na+].[CH:6]([C:8]1[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=1)=[O:7].Br[C:18]1[S:19][CH:20]=[CH:21][N:22]=1>O.COCCOC.C(OCC)(=O)C.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>[S:19]1[CH:20]=[CH:21][N:22]=[C:18]1[C:11]1[CH:12]=[CH:13][C:8]([CH:6]=[O:7])=[CH:9][CH:10]=1

Participants

8

Reactant 3

HCID 764302-BromothiazoleHCID 516892Sodium BicarbonateHCID 5910734-Formylphenylboronic Acid

Product 1

HCID 105356554-(1,3-Thiazol-2-yl)benzaldehydeYield 35%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of NaHCO3 (3.83 g, 45.6 mmol) and 4-formylphenylboronic acid (2.69 g, 18.0 mmol) in water (60 mL) was added to a solution of 2-bromothiazole (2.50 g, 15.2 mmol) and tetrakis(triphenylphosphine)palladium(0) (500 mg, 0.43 mmol) in DME (60 mL). The reaction mixture was heated to reflux for 18 h, cooled to room temperature, diluted with ethyl acetate, washed with sat. aq. NaHCO3 and brine, dried with Na2SO4, and concentrated in vacuo. Two consecutive recrystallizations from hexanes/ethyl acetate yielded 998 mg (35%) of the title compound. MS 190 (M+H)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 18 h
  3. washwashed with sat. aq. NaHCO3 and brine
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated in vacuo
  6. customTwo consecutive recrystallizations from hexanes/ethyl acetate

Sources & evidence

ORD record
ord-37d5b92c8caa4a9597b6f56bf1abdb17
Source dataset
uspto-grants-2004_11
Patent number
US06825170B2

Reaction notes

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