Bromine → 2-Bromo-1-(3-methoxy-4-pyridin-2-ylphenyl)propan-1-one

HRID 2213109Notes

Reaction equation

HRID 2213109 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15](=[O:18])[CH2:16][CH3:17])[CH:6]=[CH:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.[Br:19]Br.C([O-])(O)=O.[Na+]>C1C=CC=CC=1.Br.C(O)(=O)C>[Br:19][CH:16]([CH3:17])[C:15]([C:5]1[CH:6]=[CH:7][C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:18]

Participants

6

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 219565211-(3-Methoxy-4-pyridin-2-ylphenyl)propan-1-one

Product 1

HCID 219565192-Bromo-1-(3-methoxy-4-pyridin-2-ylphenyl)propan-1-one

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Procedure

A solution of 1-(3-methoxy-4-pyridin-2-ylphenyl)propan-1-one (120 mg, 0.5 mmol) in benzene (1 mL) and 30% HBr/Acetic acid (1 mL) was cooled to 0° C. and was treated with a solution of bromine (0.024 mL, 0.5 mmol) in benzene (0.5 mL) over 1 h. The reaction was stirred for an additional 30 min, then poured into an iced solution of saturated aqueous NaHCO3 (100 mL), and the product was extracted into ethyl acetate (3×50 mL). The combined organic layers were dried (MgSO4) and concentrated to afford 2-bromo-1-(3-methoxy-4-pyridin-2-ylphenyl)propan-1-one.

Workup

  1. extractionthe product was extracted into ethyl acetate (3×50 mL)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4228a22cbaae4d809f075933df9d3f6a
Source dataset
uspto-grants-2006_09
Patent number
US07105533B2

Reaction notes

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