N-(4-fluorophenyl)acetamide → HCID 59437302, compound

HRID 244467

Reaction equation

HRID 244467 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:13])[CH3:12])=[CH:6][CH:5]=1.[Br:14][C:15]1[CH:20]=[CH:19][C:18](F)=[C:17]([N+:22]([O-:24])=[O:23])[CH:16]=1>C1COCC1>[Br:14][C:15]1[CH:20]=[CH:19][C:18]([N:10]([C:7]2[CH:6]=[CH:5][C:4]([F:3])=[CH:9][CH:8]=2)[C:11](=[O:13])[CH3:12])=[C:17]([N+:22]([O-:24])=[O:23])[CH:16]=1

Participants

5

Reactant 3

HCID 9601N-(4-fluorophenyl)acetamideHCID 24758Sodium hydrideHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 59437302HCID 59437302, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a room temperature suspension of sodium hydride (33.4 mmol, 1.34 g of 60% in mineral oil) in 60 mL of THF was added a solution of the N-(4-fluorophenyl)acetamide (4.1 g, 26.8 mmol) in THF (30 mL) over a 5 minute period. After 30 minutes, a solution of 4-bromo-1-fluoro-2-nitrobenzene (3.2 mL, 26.8 mmol) in THF (10 mL) was added. After 15 hours, the reaction was concentrated in vacuo, the residue was diluted with 1 N sulfuric acid (300 mL) and extracted with three 100 mL portions of methylene chloride. The combined organic layers were washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo to afford a brownish oil. The residue was purified by column chromatography over silica gel eluting with 0-100% ethyl acetate in hexanes to afford 3.7 g of N-(4-bromo-2-nitrophenyl)-N-(4-fluorophenyl)acetamide as a thick yellow oil. MS m/z 353/355 (MH+).

Workup

  1. waitAfter 15 hours
  2. concentrationthe reaction was concentrated in vacuo
  3. additionthe residue was diluted with 1 N sulfuric acid (300 mL)
  4. extractionextracted with three 100 mL portions of methylene chloride
  5. washThe combined organic layers were washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto afford a brownish oil
  9. customThe residue was purified by column chromatography over silica gel eluting with 0-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-5835df7ae1a34871b3b3f4832d9ce855
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Linked notes

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