Sodium Carbonate → 2'-Methoxy-5'-methyl-3-nitro-biphenyl-3-carboxylic acid

HRID 384325Notes

Reaction equation

HRID 384325 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1OC.[C:14]([C:17]1[CH:18]=C(B(O)O)[CH:20]=[CH:21][CH:22]=1)(O)=O.[C:26](=[O:29])([O-])[O-:27].[Na+].[Na+].[O:32]1CCOC[CH2:33]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>[CH3:33][O:32][C:20]1[CH:21]=[CH:22][C:17]([CH3:14])=[CH:18][C:8]=1[C:6]1[CH2:5][C:4]([N+:9]([O-:11])=[O:10])([C:26]([OH:27])=[O:29])[CH:3]=[CH:2][CH:7]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 27339573-Carboxyphenylboronic acidHCID 138601831-Bromo-2-methoxy-5-methyl-3-nitrobenzene

Product 1

HCID 866488982'-Methoxy-5'-methyl-3-nitro-biphenyl-3-carboxylic acidYield 88.1%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

1-Bromo-2-methoxy-5-methyl-3-nitro-benzene 11c (15.0 g, 61 mmol) and 3-carboxyphenylboronic acid (11.6 g, 70.1 mmol) were dissolved in 200 mL of 1,4-dioxane followed by addition of tetrakis(triphenylphosphine)palladium (2.8 g, 2.44 mmol) and 61 mL of aqueous sodium carbonate (12.9 g, 122 mmol). The reaction mixture was heated to reflux overnight. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was concentrated under reduced pressure and the residue was diluted with 500 mL of water. The mixture was washed with the solvent mixture of 150 mL of n-hexane and 150 mL of ethyl acetate followed by ethyl acetate (300 mL×2). The aqueous layer was adjusted to pH 1˜2 with concentrated hydrochloric acid. The mixture was filtered and the filter cake was dried to obtain the title compound 2′-methoxy-5′-methyl-3-nitro-biphenyl-3-carboxylic acid 11d (15.4 g, 88.1%) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight
  3. concentrationThe mixture was concentrated under reduced pressure
  4. additionthe residue was diluted with 500 mL of water
  5. washThe mixture was washed with the solvent mixture of 150 mL of n-hexane and 150 mL of ethyl acetate
  6. filtrationThe mixture was filtered
  7. customthe filter cake was dried

Sources & evidence

ORD record
ord-ee89d91c3c1848c4972772c211ca95af
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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