N-bromobutanimide → Methyl 3-bromo-5-formylbenzoate

HRID 1497979Notes

Reaction equation

HRID 1497979 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=[O:2].[Br:13]N1C(=O)CCC1=O>S(=O)(=O)(O)O>[Br:13][C:11]1[CH:10]=[C:5]([CH:4]=[C:3]([CH:1]=[O:2])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 639145Methyl 3-formylbenzoate

Product 1

HCID 11436457Methyl 3-bromo-5-formylbenzoate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a mixture of methyl 3-formylbenzoate (5.0 g, 30.5 mmol) in concentrated sulfuric acid (50 mL) was added N-bromosuccinimide (5.4 g, 30.5 mmol) in one portion at 0° C. After warming to room temperature, the reaction mixture was stirred for 2 days before being poured into 400 mL of ice/water. Once the ice had melted, the aqueous phase was extracted with DCM (2×400 mL). The combined organic phases were passed through a hydrophobic fit. The solvent was removed in vacuo and the residue was purified via silica gel chromatography, eluting with 0-10% EtOAc in isohexane, to give the title compound as an oil that solidified upon standing (4.6 g, 63%). 1H NMR (400 MHz, CDCl3): δ 10.02 (s, 1H), 8.45 (t, J=1.5 Hz, 1H), 8.41 (t, J=1.7 Hz, 1H), 8.20 (t, J=1.7 Hz, 1H), 3.98 (s, 3H).

Workup

  1. extractionthe aqueous phase was extracted with DCM (2×400 mL)
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified via silica gel chromatography
  4. washeluting with 0-10% EtOAc in isohexane

Sources & evidence

ORD record
ord-7d3278564b644aa692095cd42710f190
Source dataset
uspto-grants-2015_12
Patent number
US09199980B2

Reaction notes

Loading…