1,2-Diiodoethane → HCID 58065000, compound

HRID 400713Notes

Reaction equation

HRID 400713 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=2)[CH:12]=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[I:23]CCI.[NH4+].[Cl-]>CCCCC.C(OCC)C.COCCOC>[C:1]([O:5][C:6]([NH:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=2)[C:12]([I:23])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 122241,2-DiiodoethaneHCID 25517Ammonium ChlorideHCID 58065015HCID 58065015, compound

Product 1

HCID 58065000HCID 58065000, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8003PentaneSolventHCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

t-Buthyllithium (2.7 mL of a 1.7 M solution in pentane, 4.61 mmol) was added to a solution of 1-(N-tert-Butoxycarbonylamino)-6,7-dimethoxynaphthalene (0.50 g, 1.65 mmol) in dry diethyl ether (5.0 mL) and dry DME (2.5 mL) at −40° C. under nitrogen. The resulting mixture was stirred at −20° C. for 5 h and then cooled to −78° C. A solution of 1,2-diiodoethane (1.30 g, 4.61 mmol) in dry DME was added and the resulting solution was allowed to warm to ambient temperature over several hours. Aq. NH4Cl was added, and the mixture was extracted twice with DCM. The combined organic extracts were washed with water, dried, filtered and evaporated to leave a dark glass. The compound was purified by column chromatography to give the pure product 1-(N-tert-Butoxycarbonylamino)-6,7-dimethoxy-4-iodonaphthalene. 1H NMR (200 MHz) (DMSO-d6) δ 1.51 (s, 9H), 3.82 (s, 3H), 3.97 (s, 3H), 7.42 (t, J=8.5 Hz, 1H), 7.48 (s, 1H), 7.57 (d, J=8.5 Hz, 1H), 7.79 (d, J=8.5 Hz, 1H), 9.28 (s, 1H).

Workup

  1. temperaturecooled to −78° C
  2. temperatureto warm to ambient temperature over several hours
  3. extractionthe mixture was extracted twice with DCM
  4. washThe combined organic extracts were washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customto leave a dark glass
  9. customThe compound was purified by column chromatography

Sources & evidence

ORD record
ord-a8c3e32816914f15acf020222e4a7408
Source dataset
uspto-grants-2014_06
Patent number
US08741917B2

Reaction notes

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