Hydrochloric Acid → 3-Fluoro-2-iodoaniline hydrochloride

HRID 620715Notes

Reaction equation

HRID 620715 reaction equation
[I:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:9]([O-])=O.[OH-].[Na+].[ClH:14]>O1CCCC1>[ClH:14].[I:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 234335971-Fluoro-2-iodo-3-nitrobenzene

Product 1

HCID 200290923-Fluoro-2-iodoaniline hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-iodo-3-fluoronitrobenzene (27.0 g, 0.101 mol) in tetrahydrofuran (200 mL) was added dropwise over a 10 minute period to a stirring solution of stannous chloride dihydrate (68.0 g, 0.302 mol) in concentrated hydrochloric acid (200 mL). After 3 hours at room temperature the reaction was poured onto ice, made alkaline (pH 11) with 50% NaOH, and extracted with diethyl ether. The combined organic phases were washed with water, brine, dried (MgSO4), filtered, and concentrated to almost dryness. Ethereal HCl was added (pH 1-2), and the resulting precipitate filtered and dried to afford 25.0 g of the title compound, m.p. 197°-198° C. (dec.).

Workup

  1. additionAfter 3 hours at room temperature the reaction was poured onto ice
  2. extractionextracted with diethyl ether
  3. washThe combined organic phases were washed with water, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to almost dryness
  7. additionEthereal HCl was added (pH 1-2)
  8. filtrationthe resulting precipitate filtered
  9. customdried

Sources & evidence

ORD record
ord-356b4f208dc04fcabb5aa2adf0ee232e
Source dataset
uspto-grants-1989_04
Patent number
US04822781

Reaction notes

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