Sodium Carbonate → HCID 14971299, compound

HRID 466183Notes

Reaction equation

HRID 466183 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][C:8]([CH:11]=[O:12])=[CH:7][C:6]=2[CH:13]=1.[C:14]1(B(O)O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.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>[C:14]1([C:2]2[CH:3]=[CH:4][C:5]3[O:10][CH2:9][C:8]([CH:11]=[O:12])=[CH:7][C:6]=3[CH:13]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 424272H-1-Benzopyran-3-carboxaldehyde, 6-bromo-HCID 66827Phenylboronic Acid

Product 1

HCID 14971299HCID 14971299, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

The starting material is prepared as follows: 6-Bromo-2H-1-benzopyran-3-carboxaldehyde (5.00 g, 20.9 mmol), phenylboronic acid (2.81 g, 23.1 mmol), and tetrakis(triphenylphosphine)palladium(0) (725 mg, 0.63 mmol) are dissolved in 50 ml of toluene and treated with 25 ml of aqueous 2M sodium carbonate under nitrogen. The mixture is heated at reflux for 6 hours. The reaction mixture is cooled and extracted with ether (3×). The combined ethereal extracts are dried (MgSO4) and evaporated. Flash chromatography (silica gel, 5% ethyl acetate/hexane), yields 6-phenyl-2H-1-benzopyran-3-carboxaldehyde, m.p. 108°-110° C., which is converted to the final product as described above.

Workup

  1. customThe starting material is prepared
  2. temperatureThe mixture is heated
  3. temperatureat reflux for 6 hours
  4. temperatureThe reaction mixture is cooled
  5. extractionextracted with ether (3×)
  6. dry with materialThe combined ethereal extracts are dried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-b29d37e2ee2f49f98f5628bb8e182e83
Source dataset
uspto-grants-1992_10
Patent number
US05155130

Reaction notes

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