Sodium Hydroxide → 2-Chloro-6-iodo-4-(trifluoromethyl)aniline

HRID 1037793Notes

Reaction equation

HRID 1037793 reaction equation
[I:1]Cl.[Cl:3][C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:5]=1[NH2:14].[OH-].[Na+]>Cl.O>[Cl:3][C:4]1[CH:9]=[C:8]([C:10]([F:12])([F:13])[F:11])[CH:7]=[C:6]([I:1])[C:5]=1[NH2:14]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24640Iodine chlorideHCID 1620012-Chloro-4-trifluoromethylaniline

Product 1

HCID 565876962-Chloro-6-iodo-4-(trifluoromethyl)anilineYield 97.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

Iodine monochloride (17.2 g, 108 mmol) in hydrochloric acid (36%, 21.4 g) and water (35 mL) was added dropwise to 2-chloro-4-(trifluoromethyl)benzenamine (20.0 g, 102 mmol) in hydrochloric acid (36%, 20.7 g) and water (140 mL). The mixture was warmed to 50° C. for a total of 8 h. Sodium hydroxide (50%, 33.5 g, 419 mmol) was added to the mixture at room temperature. The mixture was extracted with dichloromethane (2×250 mL), and the extracts were dried and evaporated to give the product as an oil (31.83 g, 97% yield).

Workup

  1. extractionThe mixture was extracted with dichloromethane (2×250 mL)
  2. customthe extracts were dried
  3. customevaporated

Sources & evidence

ORD record
ord-d3eda9272e92406abb9d60be17ad1a3e
Source dataset
uspto-grants-2013_10
Patent number
US08546618B2

Reaction notes

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