p-Fluoronitrobenzene → HCID 22728659, compound

HRID 2084997Notes

Reaction equation

HRID 2084997 reaction equation
C(=O)([O-])[O-].[K+].[K+].[SH:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([OH:13])=[O:12].[N+:17]([C:20]1[CH:25]=[CH:24][C:23](F)=[CH:22][CH:21]=1)([O-:19])=[O:18].C(=O)(O)[O-].[Na+]>CC(C)=O>[N+:17]([C:20]1[CH:25]=[CH:24][C:23]([S:7][C:8]2[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=2)[C:11]([OH:13])=[O:12])=[CH:22][CH:21]=1)([O-:19])=[O:18]

Participants

6

Reactant 4

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 95737Benzoic acid, 3-mercapto-HCID 516892Sodium Bicarbonate

Product 1

HCID 22728659HCID 22728659, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of potassium carbonate (18 g) in acetone (140 mL) at ambient temperature was treated with 3-mercaptobenzoic acid (10 g, 64.4 mmol, 1 eq) followed by 4-nitrofluorobenzene (18 g, 127.7 mmol, 2 eq). The resultant mixture was stirred for 18 h and then poured onto saturated sodium bicarbonate and washed with ethyl acetate. The basic aqueous layer was acidified with SN HCl and extracted into ethyl acetate (3×100 mL). The combined organics were dried with anhydrous sodium sulphate and concentrated in vacuo to give the product as a solid.

Workup

  1. washwashed with ethyl acetate
  2. extractionextracted into ethyl acetate (3×100 mL)
  3. dry with materialThe combined organics were dried with anhydrous sodium sulphate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9c37909ed2f44b16a443bdc0f829f13f
Source dataset
uspto-grants-2004_04
Patent number
US06719520B2

Reaction notes

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