Potassium Carbonate → 864866-56-8

HRID 500251Notes

Reaction equation

HRID 500251 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)=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-6f8ca78b602d404f8c77655edc882233
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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