Iodine → HCID 58764266, compound

HRID 2387046Notes

Reaction equation

HRID 2387046 reaction equation
[I:1]I.[CH2:3]([O:10][C:11]1[C:16]([CH2:17][C:18]([F:21])([F:20])[F:19])=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:22])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(Cl)(Cl)Cl.FC(F)(F)C([O-])=O.[Ag+]>[CH2:3]([O:10][C:11]1[C:16]([CH2:17][C:18]([F:20])([F:19])[F:21])=[CH:15][C:14]([I:1])=[CH:13][C:12]=1[CH3:22])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 807IodineHCID 58764188HCID 58764188, compound

Product 1

HCID 58764266HCID 58764266, compound

Reagents, catalysts & solvents 2

HCID 76299Silver trifluoroacetateCatalystHCID 6212ChloroformSolvent2×

Procedure

A solution of iodine (1.52 g, 6.0 mmol) dissolved in CHCl3 (80 mL) was added dropwise to a stirred mixture of 2-benzyloxy-1-methyl-3-(2,2,2-trifluoro-ethyl)-benzene (2.1 g, 6.0 mmol), silver trifluoroacetate (1.33 g, 6.0 mmol) in CHCl3 (20 mL). After the addition was complete the reaction mixture was stirred for 1 hour. The mixture was filtered through a pad of celite washing with CH2Cl2. The filtrate was washed with satd Na2S2O3, brine, dried over Na2SO4 and concentrated to a pale yellow solid (1.68 g). LCMS: APCI−VE=405

Workup

  1. additionAfter the addition
  2. filtrationThe mixture was filtered through a pad of celite
  3. washwashing with CH2Cl2
  4. washThe filtrate was washed with satd Na2S2O3, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to a pale yellow solid (1.68 g)

Sources & evidence

ORD record
ord-0a29eb637bad44c4b95a8a3869200e75
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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