Water → HCID 18333609, compound

HRID 2269217Notes

Reaction equation

HRID 2269217 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][SH:19])=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+].O>CC(C)=O>[F:1][C:2]1[CH:7]=[C:6]([S:19][CH2:18][C:17]2[CH:20]=[CH:21][C:14]([O:13][CH3:12])=[CH:15][CH:16]=2)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[F:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([S:19][CH2:18][C:17]2[CH:20]=[CH:21][C:14]([O:13][CH3:12])=[CH:15][CH:16]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 679672,4-DifluoronitrobenzeneHCID 804074-Methoxy-alpha-toluenethiol

Product 2

HCID 18333609HCID 18333609, compoundHCID 18333614HCID 18333614, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2,4-difluoronitrobenzene (2.6 ml, 23.3 mmol), p-methoxybenzyl mercaptan (2.00 g, 11.7 mmol), K2CO3 (6.47 g, 46.8 mmol) in acetone (50 ml) was refluxed for 20 h. The reaction mixture was poured into cold water. The whole was extracted with CH2Cl2 (3×100 ml), and the combined organic layers were dried (Na2SO4), filtered, and concentrated. The residue was purified by flash chromatography (1:30→1:20 EtOAc/hexanes) to give the desired 2-fluoro-4-(4′-methoxybenzylmercapto)nitrobenzene containing a small amount of 4-fluoro-2-(4′-methoxybenzylmercapto)nitrobenzene. MS (Cl) m/e 294 (M+H)+.

Workup

  1. temperaturewas refluxed for 20 h
  2. extractionThe whole was extracted with CH2Cl2 (3×100 ml)
  3. dry with materialthe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (1:30→1:20 EtOAc/hexanes)

Sources & evidence

ORD record
ord-ff57c858d2a64350908873dfc1ca10be
Source dataset
uspto-grants-2001_12
Patent number
US06329395B1

Reaction notes

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