Potassium Carbonate → 4-(2-Nitro-4-phenoxymethyl-phenylsulfanyl)-phenol

HRID 2197984Notes

Reaction equation

HRID 2197984 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17].[SH:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N+:16]([C:3]1[CH:4]=[C:5]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:7][C:2]=1[S:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2401474-MercaptophenolHCID 684618561-Bromo-2-nitro-4-phenoxymethyl-benzene

Product 1

HCID 684589784-(2-Nitro-4-phenoxymethyl-phenylsulfanyl)-phenolYield 84.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from Example 221b (0.16 g, 0.52 mmol) was reacted with 90% 4-mercapto-phenol (0.073 g, 0.52 mmol) in DMF at 80° C. under nitrogen in the presence of potassium carbonate (0.126 g, 0.91 mmol). The reaction was quenched after 18 h by pouring into dilute HCl and extraction with ether. The combined extracts were dried over MgSO4, filtered and concentrated under vacuum giving the crude title compound. The crude product was purified by flash chromatography on silica gel eluting with EtOAc-hexanes to give the title compound (0.155 g, 84%).

Workup

  1. customThe reaction was quenched after 18 h
  2. additionby pouring into dilute HCl and extraction with ether
  3. dry with materialThe combined extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customgiving the crude title compound
  7. customThe crude product was purified by flash chromatography on silica gel eluting with EtOAc-hexanes

Sources & evidence

ORD record
ord-67855ede8354459096b4a05fca1fe66a
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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