Dichloromethane → Methyl 2-[(4-chloro-2-nitrophenyl)thio]benzoate

HRID 2109901Notes

Reaction equation

HRID 2109901 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6](F)[CH:7]=1.[C:12]([O:21][CH3:22])(=[O:20])[C:13]1[C:14](=[CH:16][CH:17]=[CH:18][CH:19]=1)[SH:15].C([O-])([O-])=O.[Cs+].[Cs+].C(Cl)[Cl:30]>CN(C=O)C>[CH3:22][O:21][C:12](=[O:20])[C:13]1[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=1[S:15][C:6]1[CH:7]=[CH:2][C:3]([Cl:30])=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 696914-Chloro-2-fluoro-1-nitrobenzene

Product 1

HCID 16762830Methyl 2-[(4-chloro-2-nitrophenyl)thio]benzoateYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-chloro-2-nitrofluorobenzene (176 mg, 1 mmol) and methyl thiosalicylate (275 μL, 2 mmol) in DMF (5 mL) was added Cs2CO3 (652 mg, 2 mmol) and the resulting mixture was stirred at room temperature for 2 h. The mixture was diluted with CH2Cl2, washed with water, dried (Na2SO4), concentrated and flash chromatographed (SiO2, heptane:toluene, 1:10-1:4) to give 300 mg (92%) of the title compound (189JO09). 1H NMR (CDCl3) δ 8.15 (d, 1 H J=2.4 Hz), 7.94 (m, 1 H), 7.53-7.46 (m, 3 H), 7.34 (dd, 1 H, 2.4, 8.6 Hz), 6.95 (d, 1 H, J=8.8 Hz), 3.82 (s, 3 H).

Workup

  1. washwashed with water
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customflash chromatographed (SiO2, heptane:toluene, 1:10-1:4)

Sources & evidence

ORD record
ord-ddeed472e80d424c88df92dadb006ac8
Source dataset
uspto-grants-2009_04
Patent number
US07517871B2

Reaction notes

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