Sodium Carbonate → 5-(2-Formylphenyl)-1,3-benzodioxole-4-carbaldehyde

HRID 42687

Reaction equation

HRID 42687 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:5]2[O:6][CH2:7][O:8][C:4]=2[C:3]=1[CH:11]=[O:12].C([O-])([O-])=O.[Na+].[Na+].[CH:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1B(O)O)=[O:20]>COC(OC)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>[CH:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:2]1[CH:10]=[CH:9][C:5]2[O:6][CH2:7][O:8][C:4]=2[C:3]=1[CH:11]=[O:12])=[O:20]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2921892-Formylphenylboronic acidHCID 110316405-Bromo-1,3-benzodioxole-4-carboxaldehyde

Product 1

HCID 584843475-(2-Formylphenyl)-1,3-benzodioxole-4-carbaldehyde

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 107951,1-DimethoxyethaneSolvent

Procedure

To a solution of 5-bromo-1,3-benzodioxole-4-carbaldehyde (0.458 g, 2.00 mmol) in dry dimethoxy-ethane were added Pd(PPh3)4 (5 mol %, 0.10 mmol), 2.5 ml 2M Na2CO3 and 2-formylphenylboronic acid (0.450 g, 3.00 mmol) under argon. The reaction mixture was heated under reflux until the starting material was consumed (monitored by TLC). Then the mixture was poured onto ice-water (30 ml) and the aqueous phase was extracted with dichloromethane (3×30 ml). The combined organic phases were dried over anhydrous MgSO4. The solvent was evaporated in vacuo and the crude product was purified by column chromatography with a mixture of hexane:ethyl acetate (9:1) as the eluent.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux until the starting material
  3. customwas consumed (monitored by TLC)
  4. additionThen the mixture was poured onto ice-water (30 ml)
  5. extractionthe aqueous phase was extracted with dichloromethane (3×30 ml)
  6. dry with materialThe combined organic phases were dried over anhydrous MgSO4
  7. customThe solvent was evaporated in vacuo
  8. customthe crude product was purified by column chromatography with a mixture of hexane:ethyl acetate (9:1) as the eluent

Sources & evidence

ORD record
ord-46f3efd3a7974c08b630dc2ecfbda700
Source dataset
uspto-grants-2013_09
Patent number
US08536210B2

Linked notes

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