1-Chloro-4-nitrobenzene → HCID 12080910, compound

HRID 1836070Notes

Reaction equation

HRID 1836070 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[OH:11][C:12]1[CH:13]=[C:14]([C:22]([O:24][CH3:25])=[O:23])[CH:15]=[C:16]([CH:21]=1)[C:17]([O:19][CH3:20])=[O:18].C(=O)([O-])[O-].[K+].[K+]>[I-].[K+].CN(C=O)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([O:11][C:12]2[CH:21]=[C:16]([C:17]([O:19][CH3:20])=[O:18])[CH:15]=[C:14]([CH:13]=2)[C:22]([O:24][CH3:25])=[O:23])=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

6

Reactant 3

HCID 74741-Chloro-4-nitrobenzeneHCID 11430Potassium CarbonateHCID 830651,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl ester

Product 1

HCID 12080910HCID 12080910, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
122.5 °C

Procedure

A mixture of 1-chloro-4-nitrobenzene (47.1 g, 0.30 mole), dimethyl 5-hydroxyisophthalate (63.0 g, 0.30 mole), anhydrous potassium carbonate (41.4 g), potassium iodide (0.2 g) and DMF (200 mL) was heated at 120-125° C. for 1.5 hours, under a slow nitrogen sweep allowing some distillate to be removed (about 75 mL) via a Dean-Stark trap. Additional DMF (50 mL) was added back to the reaction mixture and heating continued for an additional 1.5 hours while an additional amount of distillate (25 mL) was allowed to collect in the Dean-Stark trap. The reaction mixture was allowed to cool to about 45° C. A heavy slurry of pale yellow product resulted which was diluted further by the addition of an ice-water mixture (350 g) with good stirring. Filtration followed by washing with water and drying in air gave the pale yellow dimethyl 5-(4-nitrophenoxy)isophthalate (90.7 g) (structure supported by FDMS) which was used in Example 12c.

Workup

  1. customto be removed (about 75 mL) via a Dean-Stark trap
  2. additionAdditional DMF (50 mL) was added back to the reaction mixture
  3. temperatureheating
  4. customto collect in the Dean-Stark trap
  5. temperatureto cool to about 45° C
  6. customA heavy slurry of pale yellow product resulted which
  7. filtrationFiltration
  8. washby washing with water
  9. customdrying in air

Sources & evidence

ORD record
ord-3d8b2b3fcfa249c7b6e34400bef8171f
Source dataset
uspto-grants-2004_08
Patent number
US06776930B2

Reaction notes

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