Iodine → HCID 87213766, compound

HRID 1782608Notes

Reaction equation

HRID 1782608 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>C1COCC1.C(OCC)C.S([O-])([O-])(=O)=S.[Na+].[Na+]>[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 3

HCID 807IodineHCID 66953855HCID 66953855, compoundHCID 178418339Butyllithium

Product 1

HCID 87213766HCID 87213766, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×HCID 24477Sodium ThiosulfateSolvent

Conditions

Temperature
-75 °C

Procedure

To a solution of 1-chloro-3,5-difluoro-2-methoxybenzene (2.0 g, 0.01 mol) in THF at −75° C. was added n-butyl lithium (2.5M in hexanes 6.7 mL) and the resulting solution was stirred at −75° C. for 1 hour. A solution of iodine (5.1 g, 0.02 mol) in THF (10 mL) was added and the reaction mixture was allowed to warm to ambient temperature. The reaction mixture was diluted with ethyl ether (50 mL) and aqueous sodium thiosulfate (10%, 50 mL) was added and stirred for 1 hour. After separating the phases, the organic phase was dried (Na2SO4) and concentrated to give 1-chloro-3,5-difluoro-4-iodo-2-methoxybenzene as a white solid: mp 62-64° C.

Workup

  1. temperatureto warm to ambient temperature
  2. additionwas added
  3. stirringstirred for 1 hour
  4. customAfter separating the phases
  5. dry with materialthe organic phase was dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ef75023a8fa04d738e1b8f3f4b2cb0d7
Source dataset
uspto-grants-2009_03
Patent number
US07498468B2

Reaction notes

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