3-Carboxyphenylboronic acid → 2'-Methoxy-3'-nitrobiphenyl-3-carboxylic acid

HRID 384286Notes

Reaction equation

HRID 384286 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[O:11][CH3:12].[C:13]([C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1)([OH:15])=[O:14]>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>[CH3:12][O:11][C:3]1[C:4]([N+:8]([O-:10])=[O:9])=[CH:5][CH:6]=[CH:7][C:2]=1[C:20]1[CH:19]=[CH:18][CH:17]=[C:16]([C:13]([OH:15])=[O:14])[CH:21]=1

Participants

6

Reactant 2

HCID 27339573-Carboxyphenylboronic acidHCID 225057131-Bromo-2-methoxy-3-nitrobenzene

Product 1

HCID 98567672'-Methoxy-3'-nitrobiphenyl-3-carboxylic acidYield 197.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
105 °C

Procedure

1-Bromo-2-methoxy-3-nitro-benzene 1c (23.25 g, 0.10 mol), 3-carboxyphenylboronic acid (19.5 g, 0.117 mol) and tetrakis(triphenylphosphine)palladium (8.86 g, 7.7 mol) were dissolved in a solvent mixture of 100 mL of 2 N aqueous sodium carbonate and 500 mL of 1,4-dioxane. The reaction mixture was heated to reflux at 105° C. for 43 hours. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was concentrated under reduced pressure and then 300 mL of 6 N hydrochloric acid and 400 mL of ethyl acetate were added. The aqueous layer was extracted with ethyl acetate (200 mL×2). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to obtain the title compound 2′-methoxy-3′-nitro-biphenyl-3-carboxylic acid 1d (53.93 g) as a light yellow solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. concentrationThe mixture was concentrated under reduced pressure
  3. addition300 mL of 6 N hydrochloric acid and 400 mL of ethyl acetate were added
  4. extractionThe aqueous layer was extracted with ethyl acetate (200 mL×2)
  5. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b83127ba82f5485f9c170523c8beb86d
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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