N-bromobutanimide → 1523194-44-6

HRID 633769Notes

Reaction equation

HRID 633769 reaction equation
C([O:5][C:6]([C:8]1[CH:9]=[CH:10][C:11]([O:14][CH:15]([F:17])[F:16])=[N:12][CH:13]=1)=[CH2:7])CCC.[Br:18]N1C(=O)CCC1=O>C1COCC1.O.O>[Br:18][CH2:5][C:6]([C:8]1[CH:13]=[N:12][C:11]([O:14][CH:15]([F:17])[F:16])=[CH:10][CH:9]=1)=[O:7]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 118199865HCID 118199865, compound

Product 1

HCID 1181998661523194-44-6Yield 75.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

A solution of 100 mg (0.41 mmol) of 5-(1-butoxyvinyl)-2-difluoromethoxypyridine in 4 mL of THF/H2O (3/1: v/v) is cooled to 0° C. 74 mg (0.41 mmol) of N-bromosuccinimide are then added in a single portion. The yellow solution is stirred at 0° C. for 1 hour and then taken up in water and extracted with EtOAc. The organic phase is washed with saturated aqueous NaHCO3 solution and then with saturated NaCl solution, dried over magnesium sulfate and then evaporated to dryness. The crude product is purified by chromatography on silica gel (eluent: 20/80 EtOAc/heptane to 40/60 EtOAc/heptane over 15 minutes) to give 82 mg of 2-bromo-1-(6-difluoromethoxypyrid-3-yl)ethanone, corresponding to the following characteristics:

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase is washed with saturated aqueous NaHCO3 solution
  3. dry with materialwith saturated NaCl solution, dried over magnesium sulfate
  4. customevaporated to dryness
  5. customThe crude product is purified by chromatography on silica gel (eluent: 20/80 EtOAc/heptane to 40/60 EtOAc/heptane over 15 minutes)

Sources & evidence

ORD record
ord-f36da45fcf604d4fb0169556ec4d7c5b
Source dataset
uspto-grants-2016_04
Patent number
US09321790B2

Reaction notes

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