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

HRID 2358819Notes

Reaction equation

HRID 2358819 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-7e29494355fb46e0a4816c62827f062d
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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