Iodine → Methyl 4-(cyclohexylcarbonyl)benzoate

HRID 1520817Notes

Reaction equation

HRID 1520817 reaction equation
[Mg].II.Br[CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.CON(C)[C:14]([C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1)=[O:15]>O1CCCC1>[CH:5]1([C:14]([C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=2)=[O:15])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 807IodineHCID 7960Cyclohexyl bromideHCID 5462224MagnesiumHCID 54447022Methyl 4-[methoxy(methyl)carbamoyl]benzoate

Product 1

HCID 12007530Methyl 4-(cyclohexylcarbonyl)benzoateYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Magnesium turnings (324 mg, 13.5 mmol) were suspended in tetrahydrofuran (20 mL). A crystal of iodine was added. Bromocyclohexane (2.00 g, 12.26 mmol) was added dropwise. The mixture was refluxed for 2 hours. The mixture was then added to a −5° C. solution of methyl 4-(methoxy(methyl)carbamoyl)benzoate (456 mg, 2.04 mmol) in tetrahydrofuran (5 mL). The reaction was stirred 1 hour, maintaining an internal temperature below 0° C. The reaction was quenched with saturated ammonium chloride and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated. Purification by column chromatography gave methyl 4-(cyclohexanecarbonyl)benzoate (160 mg, 32%). 1H NMR (400 MHz, CDCl3, δ): 8.10-8.12 (m, 2H), 7.96-7.98 (m, 2H), 3.94 (s, 3H), 3.22-3.25 (m, 1H), 1.90-1.82 (m, 4H), 1.76-1.72 (m, 1H), 1.25-1.50 (m, 5H).

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. temperaturemaintaining an internal temperature below 0° C
  3. customThe reaction was quenched with saturated ammonium chloride
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by column chromatography

Sources & evidence

ORD record
ord-aa5ba80de0fd4058be6fdf4f3c246e50
Source dataset
uspto-grants-2015_07
Patent number
US09073871B2

Reaction notes

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