Iodine → HCID 13815239, compound

HRID 629844Notes

Reaction equation

HRID 629844 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 cannula 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-da2502a2fdc9479e9504dadb2f575b1c
Source dataset
uspto-grants-2016_04
Patent number
US09315527B2

Reaction notes

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