N-bromobutanimide → HCID 59560111, compound

HRID 1177316Notes

Reaction equation

HRID 1177316 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]2[O:11][CH:10]=[CH:9][C:8]2=[C:12]([C:14]([O:16][CH3:17])=[O:15])[CH:13]=1)([CH3:3])[CH3:2].C1C(=O)N([Br:25])C(=O)C1>C(Cl)(Cl)Cl>[Br:25][C:10]1[O:11][C:7]2[C:8](=[C:12]([C:14]([O:16][CH3:17])=[O:15])[CH:13]=[C:5]([O:4][CH:1]([CH3:3])[CH3:2])[CH:6]=2)[CH:9]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 59560409HCID 59560409, compound

Product 1

HCID 59560111HCID 59560111, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 6-isopropoxybenzofuran-4-carboxylate (344a) (2.17 g, 9.25 mmol) and NBS (4.12 g, 23.1 mmol) in 50 mL of CHCl3 was heated at 60° C. for 5 hrs, followed by addition of another batch of NBS (2.50 g, 14.0 mmol). After stirring for an additional 1.2 h, the reaction was concentrated, and the residue was purified with Biotage column chromatography eluting with CHCl3 to give a yellow oil (2.52 g, 87% yield). 1H NMR (400 MHz, CDCl3) δ 7.57 (d, J=2.27 Hz, 1 H) 7.22 (s, 1 H) 7.18 (d, J=2.01 Hz, 1 H) 4.56-4.64 (m, 1 H), 3.97 (s, 3H), 1.37 (d, J=6.04 Hz, 6 H); LCMS for C13H13BrO4 m/z 312.0 (M+H+).

Workup

  1. concentrationthe reaction was concentrated
  2. customthe residue was purified with Biotage column chromatography
  3. washeluting with CHCl3

Sources & evidence

ORD record
ord-f8fa27ad33ae44c58588a4792363b35d
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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