Hydrochloric Acid → HCID 22236583, compound

HRID 1743853Notes

Reaction equation

HRID 1743853 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[CH2:12]=[O:13].[OH-].[K+].Cl>CS(C)=O.C(O)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:12][OH:13])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 14797Potassium HydroxideHCID 679654-Fluoro-2-nitrotoluene

Product 1

HCID 22236583HCID 22236583, compoundYield 23.8%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4-fluoro-1-methyl-2-nitrobenzene (73.2 g, 0.47 mole) in DMSO (75 mL) was added paraformaldehyde (14.1 g, 0.47 mole), followed by potassium hydroxide (0.75 g) in ethanol (5 mL). The resulting reaction mixture was stirred at room temperature for six days and water (2 L) was added and the mixture neutralized with hydrochloric acid (2 N). The mixture was extracted with ethyl acetate (1 L) and the combined organic layers were washed with water (1 L), saturated sodium chloride (500 mL), dried (sodium sulfate) and concentrated to a yellow solid. Purification by flash column chromatography (silica gel, 1:1 methylene chloride:hexanes to methylene chloride) provided 20.7 g of the title compound as a light yellow oil. 1H NMR (CDCl3): 7.63 δ (dd, 1H); 7.40 δ (dd, 1H); 7.28 δ (dd, 1H); 3.90 δ (t, 3H); 3.10 δ (t, 2H); 1.55 δ (broad, 1H).

Workup

  1. customThe resulting reaction mixture
  2. extractionThe mixture was extracted with ethyl acetate (1 L)
  3. washthe combined organic layers were washed with water (1 L), saturated sodium chloride (500 mL)
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated to a yellow solid
  6. customPurification by flash column chromatography (silica gel, 1:1 methylene chloride:hexanes to methylene chloride)

Sources & evidence

ORD record
ord-550c2bb3785a4cd3991eab696fc4fb32
Source dataset
uspto-grants-2006_03
Patent number
US07012089B2

Reaction notes

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