Potassium Carbonate → 864866-56-8

HRID 2090471Notes

Reaction equation

HRID 2090471 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=O)=[C:4]([CH2:12]Br)[CH:3]=1.[CH:14]1([NH2:17])[CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:10][CH:11]=1)[C:6](=[O:8])[N:17]([CH:14]1[CH2:16][CH2:15]1)[CH2:12]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69828CyclopropylamineHCID 22031079Methyl 4-bromo-2-(bromomethyl)benzoate

Product 1

HCID 23158197864866-56-8Yield 94.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of methyl 4-bromo-2-(bromomethyl)benzoate (0.13 g, 0.42 mmol), cyclopropylamine (0.034 mL, 0.49 mmol) and potassium carbonate (0.090 g, 0.65 mmol) in ethanol (0.9 mL) was stirred at 40° C. for 3 h. The reaction mixture was quenched with saturated sodium bicarbonate and extracted with EtOAc (3×20 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by chromatography on silica gel with 30% EtOAc in hexanes to afford the desired product (0.10 g, 94%). LCMS (M+H)+: m/z=252.0/254.0.

Workup

  1. customThe reaction mixture was quenched with saturated sodium bicarbonate
  2. extractionextracted with EtOAc (3×20 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel with 30% EtOAc in hexanes

Sources & evidence

ORD record
ord-349d5cfef64245b7866eb679a0ae5787
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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