N-bromobutanimide → Methyl 5-(bromomethyl)-1-benzofuran-2-carboxylate

HRID 252787Notes

Reaction equation

HRID 252787 reaction equation
[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:8]=2[CH:9]=1)=[O:4].[Br:15]N1C(=O)CCC1=O.N(C1(C#N)CCCCC1)=NC1(C#N)CCCCC1>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([CH2:14][Br:15])=[CH:10][C:8]=2[CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 749781,1'-Azobis(cyclohexanecarbonitrile)HCID 13157012Methyl 5-methyl-1-benzofuran-2-carboxylate

Product 1

HCID 13662977Methyl 5-(bromomethyl)-1-benzofuran-2-carboxylateYield 96.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 583 (500 mg, 2.63 mmol), N-bromosuccinimide (561 mg, 3.15 mmol) and 1,1′-azobis(cyclohexanecarbonitrile) (Vazo) (63 mg, 0.26 mmol) in 15 ml of CCl4 was heated overnight under reflux. The mixture was cooled to room temperature, quenched by adding water and extracted with DCM. The organic layer was washed with brine and dried over MgSO4, filtered and concentrated. The crude residue was purified by column chromatography (30% ethyl acetate/hexane) to afford the title compound 585 (680 mg, 96% yield). 1H NMR: (CDCl3) δ (ppm): 7.79 (s, 1H), 7.70-7.52 (m, 3H), 4.69 (s, 2H), 4.06 (s, 3H), 3.72 (s, 2H). LRMS: 268.2 (Calc.); 269.1 (found).

Workup

  1. temperaturewas heated overnight
  2. temperatureunder reflux
  3. customquenched
  4. additionby adding water
  5. extractionextracted with DCM
  6. washThe organic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude residue was purified by column chromatography (30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-95bdfb39fb314e5ea6e56b329736a50c
Source dataset
uspto-grants-2011_01
Patent number
US07868204B2

Reaction notes

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