Potassium Iodide → 2,4-Difluoro-3-iodo-1,5-dimethoxybenzene

HRID 1052307Notes

Reaction equation

HRID 1052307 reaction equation
[F:1][C:2]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([O:11][CH3:12])=[C:5]([F:13])[C:3]=1N.N([O-])=O.[Na+].[I-:18].[K+]>Cl.O>[F:1][C:2]1[C:3]([I:18])=[C:5]([F:13])[C:6]([O:11][CH3:12])=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 102618922,6-Difluoro-3,5-dimethoxybenzenamineHCID 23668193Sodium Nitrite

Product 1

HCID 867228052,4-Difluoro-3-iodo-1,5-dimethoxybenzeneYield 72.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×

Procedure

To a stirred slurry of 2,6-difluoro-3,5-dimethoxyaniline (1.00 g, 5.29 mmol) in 6.0 M hydrogen chloride in water (9.00 mL, 54.0 mmol), a solution of sodium nitrite (0.383 g, 5.55 mmol) in water (2 mL) was added dropwise over 15 minutes at 0° C. After another 15 minutes, the resulting orange-red slurry was added to a solution of potassium iodide (3.50 g, 21.1 mmol) in water (5 mL) in small portions at 0° C. After addition, the reaction mixture was allowed to warm to room temperature and then it was stirred for 1 hour. Solid precipitated which was filtered out. The solid was washed with water and dried under vacuum to give the desired product (1.15 g, 70%). 1H NMR (400 MHz, CDCl3): δ 6.68 (t, J=8.0 Hz, 1H), 3.88 (s, 6H) ppm.

Workup

  1. additionAfter addition
  2. customSolid precipitated which
  3. filtrationwas filtered out
  4. washThe solid was washed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-8585e1d3ae324d51843e080bbdd1634c
Source dataset
uspto-grants-2016_07
Patent number
US09388185B2

Reaction notes

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