Bromine → 2-Bromo-1-(2-bromopyridin-3-YL)ethanone

HRID 589102Notes

Reaction equation

HRID 589102 reaction equation
[Br:1][C:2]1[C:7]([C:8](=[O:10])[CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[Br:11]Br>C(O)(=O)C.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[Br:11][CH2:9][C:8]([C:7]1[C:2]([Br:1])=[N:3][CH:4]=[CH:5][CH:6]=1)=[O:10]

Participants

6

Reactant 2

HCID 24408BromineHCID 99903691-(2-Bromopyridin-3-yl)ethan-1-one

Product 1

HCID 534166012-Bromo-1-(2-bromopyridin-3-YL)ethanoneYield 73.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 1-(2-bromopyridin-3-yl)ethanone (2.10 g, 10.5 mmol) in acetic acid (28.0 mL) was treated with bromine (595 μL, 11.5 mmol) and heated at 90° C. for 1 h. The reaction mixture was diluted with ethyl acetate and saturated aqueous sodium bicarbonate solution. The aqueous layer was separated and further extracted with ethyl acetate (2×80 mL). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated to give the crude product. Purification by flash column chromatography (10% ethyl acetate/hexanes to 30% ethyl acetate/hexanes) gave the desired product (2.15 g, 73%). LCMS calculated for C7H6Br2NO (M+H)+: m/z=277.9, 279.9, 281.9. found: 277.7, 279.7, 281.8.

Workup

  1. customThe aqueous layer was separated
  2. extractionfurther extracted with ethyl acetate (2×80 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude product
  8. customPurification by flash column chromatography (10% ethyl acetate/hexanes to 30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-851773c87dd84c2d9aadcd46c921f509
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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