Sodium Iodide → Benzene, 1-cyclohexyl-2-iodo-

HRID 2180694Notes

Reaction equation

HRID 2180694 reaction equation
[Na+].[I-:2].CN[C@@H]1CCCC[C@H]1NC.Br[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C(O)CCCC>[Cu]I>[I:2][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 62761-PentanolHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 109445021-Bromo-2-cyclohexylbenzene

Product 1

HCID 11335141Benzene, 1-cyclohexyl-2-iodo-Yield 99%

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
130 °C

Procedure

A Schlenk tube was charged with CuI (9.6 mg, 0.050 mmol, 5.0 mol %), NaI (300 mg, 2.00 mmol), evacuated and backfilled with argon. Racemic trans-N,N′-dimethyl-1,2-cyclohexanediamine (16 μL, 0.10 mmol, 10 mol %), 1-bromo-2-cyclohexylbenzene (97% pure; Lancaster; 186 μL, 1.00 mmol), n-pentanol (1 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 130° C. for 40 h. The resulting suspension was allowed to reach room temperature and filtered through silica gel (1×0.5 cm) eluting with hexane (50 mL). The filtrate was concentrated, and the residue was purified by flash chromatography on silica gel (hexane) to provide the known 1-iodo-2-cyclohexylbenzene (283 mg, 99% yield; ca. 97% pure) as a colorless liquid. See McGuine, T. H.; Dull, M. F. J. Am. Chem. Soc. 1947, 69, 1469. 1H NMR (400 MHz, CDCl3): δ 7.85 (dd, J=7.5, 1.2 Hz, 1H), 7.32 (td, J=7.5, 1.2 Hz, 1H), 7.23 (dd, J=7.5, 1.7 Hz, 1H), 6.90 (td, J=7.5, 1.7 Hz, 1H), 2.81 (tt, J=11.7, 3.0 Hz, 1H), 1.97-1.74 (m, 5H), 1.55-1.23 (m, 5H). 13C NMR (100 MHz, CDCl3): δ 149.3, 139.5, 128.4, 127.6, 126.6, 101.5, 48.5, 33.4, 26.8, 26.1.

Workup

  1. customevacuated
  2. customThe Schlenk tube was sealed with a Teflon valve
  3. customto reach room temperature
  4. filtrationfiltered through silica gel (1×0.5 cm)
  5. washeluting with hexane (50 mL)
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified by flash chromatography on silica gel (hexane)

Sources & evidence

ORD record
ord-faa76bcfd4d44463ac98f807d34f7eee
Source dataset
uspto-grants-2005_05
Patent number
US06888032B2

Reaction notes

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