Phenol → 4-Chloro-2-nitro-1-phenoxybenzene

HRID 883907Notes

Reaction equation

HRID 883907 reaction equation
CN(C=O)C.Br[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[N+:14]([O-:16])=[O:15].[C:17]1([OH:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])([O-])=O.[Na+].[Na+]>O>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([O:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:8]([N+:14]([O-:16])=[O:15])[CH:9]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 27949042-Bromo-5-chloronitrobenzene

Product 1

HCID 8911814-Chloro-2-nitro-1-phenoxybenzeneYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of DMF (50 mL) was added 1-bromo-2-nitro-4-chloro-benzene (5.0 g, 21.1 mmol), phenol (1.9 g, 21.1 mmol), and Na2CO3 (2.3 g, 21.1 mmol). The solution was heated to 85° C. and stirred overnight. The reaction was poured into water and extracted with EtOAc. Washed with water and dried over Na2SO4, filtered and concentrated under vacuum giving a yellow oil that was purified by silica gel column chromatography eluting with Hexanes:Ethyl Acetate (90:10) to give 4-chloro-2-nitro-1-phenoxy-benzene (3.8 g, 74%). 4-Chloro-2-nitro-1-phenoxy-benzene (13 g, 52.1 mmol) was reacted with SnCl2 (49.3 g, 260 mmol) following the procedure from Example 7f giving 5-chloro-2-phenoxy-phenylamine as a white solid 9.0 g, 79%).

Workup

  1. extractionextracted with EtOAc
  2. washWashed with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customgiving a yellow oil that
  7. customwas purified by silica gel column chromatography
  8. washeluting with Hexanes:Ethyl Acetate (90:10)

Sources & evidence

ORD record
ord-4a20a9dacb014667b24157978c2b915f
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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