Sodium Iodide → 3-Iodobenzo[b]thiophene

HRID 2253492Notes

Reaction equation

HRID 2253492 reaction equation
[Na+].[I-:2].CN[C@@H]1CCCC[C@H]1NC.Br[C:14]1[C:15]2[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=2[S:17][CH:18]=1.C1(C)C=CC=C(C)C=1>CCCCCC.[Cu]I.COCCOCCOC>[I:2][C:14]1[C:15]2[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=2[S:17][CH:18]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 7929M-XyleneHCID 123250Benzo(b)thiophene, 3-bromo-HCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine

Product 1

HCID 110972903-Iodobenzo[b]thiopheneYield 93.4%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8058HexaneSolventHCID 8150DiglymeSolvent

Conditions

Temperature
130 °C

Procedure

A Schlenk tube was charged with CuI (9.6 mg, 0.0504 mmol, 5.0 mol %/), NaI (300 mg, 2.00 mmol), evacuated and backfilled with argon. trans-N,N′-Dimethyl-1,2-cyclohexanediamine (16 μL, 0.10 mmol, 10 mol %), 3-bromobenzo[b]thiophene (131 μL, 1.00 mmol), m-Xylene (0.80 mL), and diglyme (0.20 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 130° C. for 22 h. The resulting suspension was allowed to reach room temperature, diluted with hexane (10 mL), and filtered through silica gel (2×2 cm) eluting with hexane (50 mL). The filtrate was concentrated, and the residue was purified by flash chromatography on silica gel to provide 3-iodobenzo[b]thiophene (243 mg, 93% yield) as a pale yellow liquid.

Workup

  1. customevacuated
  2. customThe Schlenk tube was sealed with a Teflon valve
  3. customto reach room temperature
  4. filtrationfiltered through silica gel (2×2 cm)
  5. washeluting with hexane (50 mL)
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-e7f8ad858e6f44c2a829d963b569e892
Source dataset
uspto-grants-2008_01
Patent number
US07323608B2

Reaction notes

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