Iodine → HCID 13815239, compound

HRID 1472931Notes

Reaction equation

HRID 1472931 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[Mg].II.[Si:15](Cl)([Cl:18])([Cl:17])[Cl:16]>C1COCC1>[C:2]1([Si:15]([Cl:18])([Cl:17])[Cl:16])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 807IodineHCID 70011-BromonaphthaleneHCID 24816Silicon tetrachlorideHCID 5462224Magnesium

Product 1

HCID 13815239HCID 13815239, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Under a dry nitrogen atmosphere, a solution of 1-bromonaphthalene (27.7 g, 0.134 mol) in THF (175 mL) was added slowly to a suspension of magnesium turnings (3.9 g, 0.16 mol) in THF (15 mL) that had previously been activated with an iodine crystal. After cooling to room temperature, this Grignard reagent was added via canula to a THF (70 mL) solution of SiCl4 (25.1 g, 0.148 mol) and stirred overnight. The mixture was evaporated to dryness, extracted with hexane and filtered to remove Mg halide. The product was distilled at 120° C. under dynamic vacuum to give a 67% yield (23.6 g, 0.0902 mol) of product. 1H NMR (CDCl3, ppm) 8.46 (dd, 1H), 8.21 (dd, J=6.8 Hz, J=1.2 Hz, 1H), 8.09 (d, J=8.4 Hz, 1H), 7.96 (d, J=7.6 Hz, 1H), 7.69 (t, 1H), 7.62 (t, 1H), 7.57 (t, 1H). 13C{1H}NMR (CDCl3, ppm) 135.51 (CH), 134.42 (C), 134.07 (CH), 133.58 (C), 129.37 (CH), 127.91 (C), 127.45 (CH), 127.16 (CH), 126.56 (CH), and 124.65 (CH). 29Si{1H} (CDCl3, ppm) −0.17 (s).

Workup

  1. customThe mixture was evaporated to dryness
  2. extractionextracted with hexane
  3. filtrationfiltered
  4. customto remove Mg halide
  5. distillationThe product was distilled at 120° C. under dynamic vacuum

Sources & evidence

ORD record
ord-95dfae45d45940ab9a8503f309c22ba6
Source dataset
uspto-grants-2015_04
Patent number
US09012673B1

Reaction notes

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