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

HRID 8972
Notes
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Reaction equation

HRID 8972 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.[K+].[K+]>C1(C)C=CC=CC=1.O.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: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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 764302-BromothiazoleHCID 5910734-Formylphenylboronic Acid

Product 1

HCID 105356554-(1,3-Thiazol-2-yl)benzaldehydeYield 15%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalyst
HCID 962
Water
Solvent
HCID 1140TolueneSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-bromothiazole (0.26 g, 1.6 mmol) and 4-formylphenylboronic acid (0.48 g, 3.2 mmol) in toluene (16 mL) was added tetrakis(triphenylphosphine)palladium(0) (0.09 g, 0.08 mmol) and K2CO3 (0.33 g, 2.4 mmol) and the solution stirred at reflux for 16 h. The reaction was cooled to room temperature, diluted with water (50 mL) and ethyl acetate (50 mL). The organic layer was separated, washed with brine (30 mL), dried (MgSO4), filtered, concentrated and purified by column chromatography on silica gel (2% MeOH/CH2Cl2) to give 4-(2-thiazolyl)-benzaldehyde (45 mg, 15%). 1H NMR (CDCl3) δ 7.45 (d, 1H, J=3.0 Hz), 7.90 (d, 1H, J=3.0 Hz), 7.97 (d, 2H, J=7.8 Hz), 8.15 (d, 2H, J=7.2 Hz), 10.07 (s, 1H (CHO)).

Workup

  1. temperatureat reflux for 16 h
  2. customThe organic layer was separated
  3. washwashed with brine (30 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by column chromatography on silica gel (2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-7a2f34a04f1b42dcbdbae8ab9077148c
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07091217B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes