N-bromobutanimide → N-[3-(5-Bromo-7-fluoro-2,3-dihydro-benzofuran-4-yl)-propyl]-acetamide

HRID 1602416Notes

Reaction equation

HRID 1602416 reaction equation
[Br:1]N1C(=O)CCC1=O.[F:9][C:10]1[C:18]2[O:17][CH2:16][CH2:15][C:14]=2[C:13]([CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:25])[CH3:24])=[CH:12][CH:11]=1>C(O)(=O)C>[Br:1][C:12]1[CH:11]=[C:10]([F:9])[C:18]2[O:17][CH2:16][CH2:15][C:14]=2[C:13]=1[CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:25])[CH3:24]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 19611636N-[3-(7-Fluoro-2,3-dihydro-benzofuran-4-yl)-propyl]-acetamide

Product 1

HCID 19611683N-[3-(5-Bromo-7-fluoro-2,3-dihydro-benzofuran-4-yl)-propyl]-acetamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

N-Bromosuccinimide (569 mg) was added to a solution of N-[3-(7-fluoro-2,3-dihydro-benzofuran-4-yl)-propyl]-acetamide (690 mg) in glacial acetic acid (15 ml) at room temperature under nitrogen and the mixture stirred for 48 h. The solution was evaporated and the residue partitioned between sodium carbonate (2N; 20 ml) and ethyl acetate (20 ml). The combined organic extracts were washed with brine (25 ml) and dried (MgSO4). The solvent was evaporated and the residue purified by column chromatography. Eluting with dichloromethane/methanol 50:1 gave the title compound as a colourlss solid (644 mg)

Workup

  1. customThe solution was evaporated
  2. customthe residue partitioned between sodium carbonate (2N; 20 ml) and ethyl acetate (20 ml)
  3. washThe combined organic extracts were washed with brine (25 ml)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated
  6. customthe residue purified by column chromatography
  7. washEluting with dichloromethane/methanol 50:1

Sources & evidence

ORD record
ord-55f7cfc9d59247a880776fb997d43fd1
Source dataset
uspto-grants-1999_11
Patent number
US05981572

Reaction notes

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