Water → 2-(5-Methyl-1,3,4-thiadiazol-2-yl)benzaldehyde

HRID 1966693Notes

Reaction equation

HRID 1966693 reaction equation
Br[C:2]1[S:3][C:4]([CH3:7])=[N:5][N:6]=1.[CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1B(O)O)=[O:9].C([O-])([O-])=O.[Na+].[Na+].O>COCCOC.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.CCOC(C)=O>[CH3:7][C:4]1[S:3][C:2]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:8]=[O:9])=[N:6][N:5]=1

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2921892-Formylphenylboronic acidHCID 71719042-Bromo-5-methyl-1,3,4-thiadiazole

Product 1

HCID 585420582-(5-Methyl-1,3,4-thiadiazol-2-yl)benzaldehydeYield 58.3%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
100 °C

Procedure

To a solution of 2-bromo-5-methyl-1,3,4-thiadiazole (150 mg, 0.84 mmol) in 1,2-dimethoxyethane (5 mL) are added 2-formylphenylboronic acid (190 mg, 1.26 mmol), Pd(PPh3)4 (97 mg, 0.08 mmol) and Na2CO3 (sat., 0.10 mL) at room temperature. The solution is heated to 100° C. for 18 hours then cooled and poured into water and EtOAc. Layers are separated and the aqueous phase extracted with EtOAc (1×10 mL). The combined organics are dried (MgSO4), filtered and concentrated to give the crude product which is purified via flash chromatography (12 g silica gel, 5-60% EtOAc/hexanes). The product-containing fractions are combined and concentrated to give 2-(5-methyl-1,3,4-thiadiazol-2-yl)-benzaldehyde (100 mg, 58%) which is used without further purification.

Workup

  1. temperaturethen cooled
  2. customLayers are separated
  3. extractionthe aqueous phase extracted with EtOAc (1×10 mL)
  4. dry with materialThe combined organics are dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude product which
  8. customis purified via flash chromatography (12 g silica gel, 5-60% EtOAc/hexanes)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-1c05207fb82b495f91e769e3370e59d3
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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