Bromine → HCID 15257067, compound

HRID 589047Notes

Reaction equation

HRID 589047 reaction equation
[Br:1]Br.[CH3:3][CH:4]([CH3:13])[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)=[O:6]>C(O)(=O)C>[Br:1][C:4]([CH3:13])([CH3:3])[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)=[O:6]

Participants

4

Reactant 2

HCID 24408BromineHCID 1010832-Methyl-1-(2-pyridyl)propan-1-one

Product 1

HCID 15257067HCID 15257067, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
105 °C

Procedure

Bromine (2.1 g, 13.4 mmol) dissolved in acetic acid (1 mL) was added slowly to a mixture of 2-methyl-(1-pyridin-2-yl)propan-1-one (2.0 g, 13 mmol) in acetic acid (20 mL) at room temperature. The reaction was heated to 105° C. for 3 h, allowed to cool to room temperature, and concentrated in vacuo to give a dark semisolid. The crude product was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The combined organic layer was washed with brine, dried over magnesium sulfate, and concentrated to give 2-bromo-2-methyl-1-(pyridin-2-yl)propan-1-one as a very dark oil (3.0 g, 98%). LCMS calculated for C9H11BrNO (M+H)+: m/z=227.9, 229.9. found: 228.1, 230.1.

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated in vacuo
  3. customto give a dark semisolid
  4. customThe crude product was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f2a6d89a5a294974a64d40c81ed4dd49
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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