1-Chloro-2-nitrobenzene → 1-[(4-Fluorophenyl)thio]-2-nitrobenzene

HRID 735194Notes

Reaction equation

HRID 735194 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.Cl[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-:18])=[O:17].[H-].[Na+]>C1COCC1>[N+:16]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[S:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 69451-Chloro-2-nitrobenzeneHCID 24758Sodium hydrideHCID 677894-Fluorothiophenol

Product 1

HCID 131536721-[(4-Fluorophenyl)thio]-2-nitrobenzeneYield 82.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-fluorothiophenol (1.0 g, 7.8 mmol) and 2-chloronitrobenzene (1.2 g, 7.8 mmol) in THF (10 mL) at 0° C. was added NaH (60% dispersion in oil, 390 mg, 9.4 mmol). The reaction was brought to room temperature and allowed to stir for 18 h. Ice was added and the layers separated. The aqueous layer was extracted three times with EtOAc (3×50 mL). The combined extracts were washed with water (50 mL) and dried (Na2SO4) and evaporated affording 4-fluorophenyl 2-nitrophenyl sulfide (1.6 g, 82%) as a yellow solid. 1H NMR (CDCl3, 300 MHz) δ 8.24 (dd, 1H, J=1.5, 8 Hz), 7.58-7.63 (m, 2H), 7.38 (dt, 1H, J=1.5, 7.4 Hz), 7.15-7.25 (m, 3H), 6.82 (dd, 1H, J=1.1, 8.1 Hz) ppm.

Workup

  1. customwas brought to room temperature
  2. additionIce was added
  3. customthe layers separated
  4. extractionThe aqueous layer was extracted three times with EtOAc (3×50 mL)
  5. washThe combined extracts were washed with water (50 mL)
  6. dry with materialdried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-d5f3a307802a425bb7c19fdfb59c303c
Source dataset
uspto-grants-2009_09
Patent number
US07592454B2

Reaction notes

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