Sodium Iodide → HCID 82277895, compound

HRID 1468225Notes

Reaction equation

HRID 1468225 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][CH:3]=1.[I-].[Na+].[H-].[Na+].[I-].Cl[CH2:19][CH2:20][S+](C)C>C(O)(C)(C)C.O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8]3([CH2:20][CH2:19]3)[C:9]2=[O:12])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 2527317-Bromo-1,2,3,4-tetrahydronaphthalen-1-oneHCID 10912030(2-Chloroethyl)diMethylsulfoniuM iodide2×

Product 1

HCID 82277895HCID 82277895, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a solution of 7-bromo-1-tetralone (1.03 g, 4.58 mmol) in tert-butanol (10 mL) was added sodium iodide (0.131 g, 0.872 mmol) and sodium hydride (0.349 g, 60% suspension in mineral oil, 8.72 mmol). The reaction mixture was stirred at r.t. for 20 min. Then (2-chloroethyl)dimethylsulfonium iodide (Intermediate 5, 1.10 g, 4.36 mmol) was added portionwise over 1 h. After the reaction had reached completion, water (15 mL) was added and the resulting mixture was extracted with EtOAc (3×15 mL). The combined organic layers were dried with sodium sulfate, filtered and concentrated in vacuo. The product was purified by flash chromatography using 5% EtOAc in heptanes as eluent to give the title compound (0.789 g, 78%). 1H NMR (400 MHz, CDCl3) δ ppm 0.84 (dd, 2 H), 1.40 (dd, 2 H), 1.95 (t, 2 H), 2.93 (t, 2 H), 7.14 (d, 1 H), 7.55 (dd, 1 H), 8.11 (d, 1 H); MS (ES+) m/z 250.98, 253.03 [M+H]+.

Workup

  1. additionwas added
  2. extractionthe resulting mixture was extracted with EtOAc (3×15 mL)
  3. dry with materialThe combined organic layers were dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-24c7a8b02a934e5ab0f5deb5b8b51587
Source dataset
uspto-grants-2015_04
Patent number
US09000184B2

Reaction notes

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