Water → 4-{4-[1-(4-Bromo-phenyl)-ethoxy]-2-nitro-phenylsulfanyl}-phenol

HRID 883922Notes

Reaction equation

HRID 883922 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:10][C:11]2[CH:16]=[CH:15][C:14](Cl)=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=2)[CH3:9])=[CH:4][CH:3]=1.[SH:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([S:21][C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=3)=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=2)[CH3:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2401474-MercaptophenolHCID 668084234-[1-(4-Bromo-phenyl)-ethoxy]-1-chloro-2-nitro-benzene

Product 1

HCID 668082204-{4-[1-(4-Bromo-phenyl)-ethoxy]-2-nitro-phenylsulfanyl}-phenolYield 68.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from Example 44B (1.15 g, 3.22 mmol) was reacted with 4-mercapto-phenol (403 mg, 3.22 mmol) and K2CO3 (890 mg, 6.44 mmol) in 25 mL of DMF at 80° C. for 18 h. Cooled to room temperature and poured into water. Extracted with CH2Cl2 and washed several times with water. Dried over Na2SO4, filtered and concentrated under vacuum giving the title compound (980 mg, 68%).

Workup

  1. extractionExtracted with CH2Cl2
  2. washwashed several times with water
  3. dry with materialDried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-accd76cb3dc04d889c1a65c15b5b877b
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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