N-bromobutanimide → HCID 59560111, compound

HRID 1643787Notes

Reaction equation

HRID 1643787 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 C13H13BrO4m/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-b8be4842694544b181b24a7cd532f82c
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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