Iodine → HCID 58764044, compound

HRID 1438191Notes

Reaction equation

HRID 1438191 reaction equation
[I:1]I.[CH2:3]([O:10][C:11]1[CH:16]=[C:15]([O:17][CH2:18][CH2:19][CH3:20])[CH:14]=[CH:13][C:12]=1[CH2:21][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[CH:16]=[C:15]([O:17][CH2:18][CH2:19][CH3:20])[C:14]([I:1])=[CH:13][C:12]=1[CH2:21][CH3:22])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 807IodineHCID 58764225HCID 58764225, compound

Product 1

HCID 58764044HCID 58764044, compound

Reagents, catalysts & solvents 2

HCID 76299Silver trifluoroacetateCatalystHCID 6212ChloroformSolvent2×

Procedure

A solution of iodine (2.82 g, 11.1 mmol) dissolved in CHCl3 (80 mL) was added dropwise to a stirred mixture of 2-benzyloxy-1-ethyl-4-propoxy-benzene (3 g, 11.1 mmol), silver trifluoroacetate (2.45 g, 11.1 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 (4.04 g, 92%). 1H NMR (400 MHz, CDCl3): δ 1.07 (t, J=7.3 Hz, 3H), 1.17 (t, J=7.6 Hz, 3H), 1.81 (m, 2H), 2.59 (q, J=7.6 Hz, 2H), 3.90 (t, J=6.3 Hz, 2H), 5.05 (s, 2H), 6.43 (s, 1H), 7.31-7.45 (m, 5H), 7.49 9s, 1H).

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 (4.04 g, 92%)

Sources & evidence

ORD record
ord-811564f9257a494aa5525be9b0913bf3
Source dataset
uspto-grants-2009_11
Patent number
US07622605B2

Reaction notes

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