N-bromobutanimide → Methyl 3-bromo-4-cyclopropylbenzoate

HRID 1487854Notes

Reaction equation

HRID 1487854 reaction equation
[CH:1]1([C:4]2[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.[Br:14]N1C(=O)CCC1=O>FC(F)(F)C(O)=O>[Br:14][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:4]=1[CH:1]1[CH2:2][CH2:3]1)[C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 11658370Methyl 4-cyclopropylbenzoate2×

Product 1

HCID 44828964Methyl 3-bromo-4-cyclopropylbenzoateYield 69.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
50 °C

Procedure

Into a 50-mL round-bottom flask, was placed a mixture of methyl 4-cyclopropylbenzoate (compound 10.1, 500 mg, 2.84 mmol), N-bromosuccinimide (500 mg, 2.81 mmol) and trifluoroacetic acid (20 mL). The mixture was stirred overnight at 50° C., then cooled and carefully quenched with water (10 mL). The mixture was extracted with ethyl acetate (3×30 mL) and the combined organic layers were washed with brine (3×30 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with petroleum ether as the eluent to yield 0.5 g (69%) of the title compound as a yellow oil.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. temperaturecooled
  3. customcarefully quenched with water (10 mL)
  4. extractionThe mixture was extracted with ethyl acetate (3×30 mL)
  5. washthe combined organic layers were washed with brine (3×30 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography with petroleum ether as the eluent

Sources & evidence

ORD record
ord-07c138283826418a84107e03cd42dbd0
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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