Phenol → Ethyl 2-nitro-5-phenoxybenzoate

HRID 1054229Notes

Reaction equation

HRID 1054229 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:13]([O-:15])=[O:14])=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].C([O-])([O-])=O.[K+].[K+].[C:22]1([OH:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C.O>[N+:13]([C:5]1[CH:4]=[CH:3][C:2]([O:28][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8])([O-:15])=[O:14]

Participants

6

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 603450Ethyl 5-chloro-2-nitrobenzoate

Product 1

HCID 57796884Ethyl 2-nitro-5-phenoxybenzoateYield 36%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

To a stirring suspension of ethyl 5-chloro-2-nitrobenzoate (15 g, 65.3 mmol) and K2CO3 (13.54 g, 98 mmol) in DMF (5 ml) was added phenol (6.76 g, 71.9 mmol). Reaction mixture was heated at 130° C. for 16 h. Reaction mixture was diluted with water and extracted with EtOAc. The organic layer was separated and distilled out to get crude product which was column purified using 10% EtOAC in hexane to get the titled compound in 36% yield.

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. distillationdistilled out
  6. customto get crude product which
  7. custompurified

Sources & evidence

ORD record
ord-b7490241d3014ddeab3ce446bfb37f76
Source dataset
uspto-grants-2016_07
Patent number
US09394300B2

Reaction notes

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