Sodium Carbonate → HCID 57483835, compound

HRID 384384Notes

Reaction equation

HRID 384384 reaction equation
O1CCOCC1.[CH3:7][O:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:12]([CH3:18])=[CH:11][C:10]=1B1OC(C)(C)C(C)(C)O1.Br[C:29]1[O:33][C:32]([C:34]([OH:36])=[O:35])=[CH:31][CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+]>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.O>[N+:15]([C:14]1[C:9]([O:8][CH3:7])=[C:10]([C:29]2[O:33][C:32]([C:34]([OH:36])=[O:35])=[CH:31][CH:30]=2)[CH:11]=[C:12]([CH3:18])[CH:13]=1)([O-:17])=[O:16]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 685115-Bromo-2-furanecarboxylic acidHCID 574838182-(2-Methoxy-5-methyl-3-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 57483835HCID 57483835, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

To a solution of the solvent mixture of 30 mL of 1,4-dioxane and 15 mL of water was added 2-(2-methoxy-5-methyl-3-nitro-phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 24a (3.1 g, 7.5 mmol) followed by 5-bromofuran-2-carboxylic acid (1.3 g, 6.8 mmol), tetrakis(triphenylphosphine)palladium (0.43 g, 0.4 mmol) and sodium carbonate (1.6 g, 15.1 mmol). The reaction mixture was heated to reflux for 1 hour. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was cooled and filtered. The filtrate was washed with ethyl acetate and concentrated under reduced pressure. The resulting residue was diluted with 50 mL of water and adjusted to pH 3 with concentrated hydrochloric acid and filtered. The filter cake was washed with ethyl acetate and dried to obtain the title compound 5-(3-nitro-2-methoxy-5-methyl-phenyl)-furan-2-carboxylic acid 46a (522 mg, 29%) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 hour
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. washThe filtrate was washed with ethyl acetate
  6. concentrationconcentrated under reduced pressure
  7. additionThe resulting residue was diluted with 50 mL of water
  8. filtrationfiltered
  9. washThe filter cake was washed with ethyl acetate
  10. customdried

Sources & evidence

ORD record
ord-cd4927aae9824edfaaafac74d55eb15d
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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