Sodium Carbonate → HCID 57483854, compound

HRID 384406Notes

Reaction equation

HRID 384406 reaction equation
[CH3:1][O:2][C:3]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=[CH:5][C:4]=1B1OC(C)(C)C(C)(C)O1.[CH3:21][O:22][C:23]([C:25]1[O:26][C:27](Br)=[CH:28][CH:29]=1)=[O:24].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.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>[CH3:21][O:22][C:23]([C:25]1[O:26][C:27]([C:4]2[CH:5]=[CH:6][CH:7]=[C:8]([N+:9]([O-:11])=[O:10])[C:3]=2[O:2][CH3:1])=[CH:28][CH:29]=1)=[O:24]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 599633Methyl 5-bromofuran-2-carboxylateHCID 574838002-(2-Methoxy-3-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 57483854HCID 57483854, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

2-(2-Methoxy-3-nitro-phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 6a (3.6 g, 12 mmol), 5-bromofuran-2-carboxylic acid methyl ester (2.05 g, 10 mmol), tetrakis(triphenylphosphine)palladium (1.55 g, 0.5 mmol) and sodium carbonate (2.12 g, 20 mmol) were dissolved in 1,4-dioxane. The reaction mixture was heated to reflux for 3 hours. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was diluted with 30 mL of water and 50 mL of ethyl acetate. The separated organic layer was concentrated under reduced pressure and recrystallized from a solvent mixture of ethyl acetate and n-hexane to obtain the title compound 5-(2-methoxy-3-nitro-phenyl)-furan-2-carboxylic acid methyl ester 54a (500 mg, yield 18%) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 hours
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionThe residue was diluted with 30 mL of water and 50 mL of ethyl acetate
  6. concentrationThe separated organic layer was concentrated under reduced pressure
  7. customrecrystallized from a solvent mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-0ea3d7d4141f47c2a4c59efef0929f4f
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

Loading…