Hydrochloric Acid → beta-Iodonaphthalene

HRID 1096733Notes

Reaction equation

HRID 1096733 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[I-:12].[K+].Cl>[Cu](I)I.CN(C)P(N(C)C)(N(C)C)=O>[I:12][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 113722-Bromonaphthalene

Product 1

HCID 136412beta-IodonaphthaleneYield 100%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
160 °C

Procedure

2-Bromonapthalene (50.0 g, 242.0 mmol), copper iodide (230.0 g, 1210.0 mmol, 5 eq.), potassium iodide (200 g, 1210.0 mmol, 5 eq.) and hexamethylphosphoramide (500 mL) were stirred and heated to 160° C. for 8 h. This was cooled and added to 1N HCl (250 mL) then toluene (300 mL) and ether (300 mL) and the mixture filtered through celite. The organic layer was separated and washed with water (2×250 mL) dried over magnesium sulphate and concentrated to afford 2-iodonaphthalene (61.5 g, 59%) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.46-7.52 (2H, m, ArH, 7.55-7.58 (1H, m, ArH), 7.68-7.74 (2H, m, ArH), 7.76-7.82 (1H, m, ArH), 8.22-8.26 (1H, m, ArH).

Workup

  1. temperatureThis was cooled
  2. filtrationtoluene (300 mL) and ether (300 mL) and the mixture filtered through celite
  3. customThe organic layer was separated
  4. washwashed with water (2×250 mL)
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-535ab3a6094f4779853b3af878ec9dfa
Source dataset
uspto-grants-2012_03
Patent number
US08138377B2

Reaction notes

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