Hydrochloric Acid → 2-(3,5-Dimethylphenyl)-4-nitrobenzoic acid

HRID 383077Notes

Reaction equation

HRID 383077 reaction equation
Br[C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[C:19]([CH3:21])[CH:20]=1.C([O-])([O-])=O.[Cs+].[Cs+].Cl>CN(C=O)C.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>[N+:11]([C:9]1[CH:8]=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([C:17]2[CH:18]=[C:19]([CH3:21])[CH:20]=[C:15]([CH3:14])[CH:16]=2)[CH:10]=1)([O-:13])=[O:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 3135342-Bromo-4-nitrobenzoic acidHCID 27343493,5-Dimethylphenylboronic acid

Product 1

HCID 234362252-(3,5-Dimethylphenyl)-4-nitrobenzoic acidYield 61.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2-Bromo-4-nitrobenzoic acid (0.43 g, 2.03 mmol) and 3,5-dimethylphenyl boronic acid (0.334 g, 2.23 mmol) were dissolved in anhydrous DMF (25 mL) under nitrogen. To this mixture was added Cs2CO3 (1.66 g, 5.08 mmol) followed by Pd(Ph3P)4 (0.12 g, 5%). The mixture was heated at 100° C. overnight. The solution was poured onto 1N HCl and extracted with Et2O. It was dried over MgSO4 and the solvent was removed in vacuo. The crude product was chromatographed on silica gel using a 9:1 mixture of hexanes and ethyl acetate to provide the desired product (0.34 g):

Workup

  1. extractionextracted with Et2O
  2. dry with materialIt was dried over MgSO4
  3. customthe solvent was removed in vacuo
  4. customThe crude product was chromatographed on silica gel using
  5. additiona 9:1 mixture of hexanes and ethyl acetate

Sources & evidence

ORD record
ord-9fa869684c304cdfb4bea89f741e232a
Source dataset
uspto-grants-2001_10
Patent number
US06310095B1

Reaction notes

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