Iodine → HCID 87213766, compound

HRID 1496878Notes

Reaction equation

HRID 1496878 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[O:10][CH3:11].C([Li])CCC.[I:17]I.OS([O-])=O.[Na+]>C1COCC1.CCOCC>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([I:17])=[C:4]([F:9])[C:3]=1[O:10][CH3:11]

Participants

7

Reactant 4

HCID 807IodineHCID 23665763Sodium BisulfiteHCID 66953855HCID 66953855, compoundHCID 178418339Butyllithium

Product 1

HCID 87213766HCID 87213766, compoundYield 92.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-72.5 °C

Procedure

2-Chloro-4,6-difluoroanisole (2.0 g, 11 mmol) was dissolved in 20 mL anhydrous THF and cooled to −70 to −75° C. 2.5M n-Butyl lithium in hexanes (6.7 mL, 17 mmol) was added dropwise. After stirring for 75 minutes at −75° C., the mixture was treated dropwise with a solution of iodine (5.1 g, 20 mmol) in 10 mL THF. After stirring for 20 minutes, the reaction solution was allowed to warm to 25° C. over 40 minutes. The reaction mixture was diluted with Et2O (50 mL) and stirred with dilute NaHSO3 solution to destroy excess iodine. The separated aqueous phase was extracted with 20 mL Et2O. The combined ether phases were washed with saturated NaCl, dried, and evaporated to give 1-chloro-3,5-difluoro-4-iodo-2-methoxybenzene (3.1 g, 91% yield): mp 62-64° C.; GC-MS (m/z=304).

Workup

  1. stirringAfter stirring for 20 minutes
  2. temperatureto warm to 25° C. over 40 minutes
  3. customto destroy excess iodine
  4. extractionThe separated aqueous phase was extracted with 20 mL Et2O
  5. washThe combined ether phases were washed with saturated NaCl
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-72bfd2563cc840ffb0f53b95a6a471fc
Source dataset
uspto-grants-2015_12
Patent number
US09199943B2

Reaction notes

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