N-bromobutanimide → 2-Bromo-1-(3-methoxy-pyridin-2-yl)-ethanone

HRID 1037674Notes

Reaction equation

HRID 1037674 reaction equation
[Br:1]N1C(=O)CCC1=O.C([O:11][C:12]([C:14]1[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[CH:16][N:15]=1)=[CH2:13])C>C1COCC1.O>[Br:1][CH2:11][C:12]([C:14]1[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[CH:16][N:15]=1)=[O:13]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 671711472-(1-Ethoxy-vinyl)-3-methoxy-pyridine

Product 1

HCID 590278252-Bromo-1-(3-methoxy-pyridin-2-yl)-ethanoneYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add N-bromo-succinimide (306 mg, 1.7 mmol) to a stirred solution of 2-(1-ethoxy-vinyl)-3-methoxy-pyridine (305 mg, 1.7 mg) in THF (30 mL) and water (2 mL). Stir for 15 mins. at RT under N2. Adsorb on SiO2 and purify by flash chromatography on silica gel eluting with 0-40% EtOAc/hexanes to afford the title compound (211 mg, 54%).

Workup

  1. customat RT
  2. custompurify by flash chromatography on silica gel eluting with 0-40% EtOAc/hexanes

Sources & evidence

ORD record
ord-ba0ae0eaa55a4c9080acaa4edca550d5
Source dataset
uspto-grants-2013_10
Patent number
US08546581B2

Reaction notes

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