Bromine → N-(5-bromo-4-fluoro-2-methoxyphenyl)acetamide

HRID 130413Notes

Reaction equation

HRID 130413 reaction equation
[Br:1]Br.[F:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:13])[CH3:12])=[C:6]([O:14][CH3:15])[CH:5]=1>C(O)(=O)C>[Br:1][C:9]1[C:4]([F:3])=[CH:5][C:6]([O:14][CH3:15])=[C:7]([NH:10][C:11](=[O:13])[CH3:12])[CH:8]=1

Participants

4

Reactant 2

HCID 24408Bromine2×HCID 60740966Acetamide, N-(4-fluoro-2-methoxyphenyl)-

Product 1

HCID 69197937N-(5-bromo-4-fluoro-2-methoxyphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (1.8 ml, 34 mmol) was added dropwise to a solution of the product of Step 1 (5.69 g, 31 mmol) in acetic acid (100 ml). After 18 hours at room temperature additional bromine (0.3 ml) was added and the solution stirred for a further 3 hours. The solution was partitioned between water and ethyl acetate and the layers separated. The organic phase was then washed with aqueous sodium thiosulfate solution, water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give the title compound. MS (ES+) m/e 262/264 [M+H]+.

Workup

  1. customThe solution was partitioned between water and ethyl acetate
  2. customthe layers separated
  3. washThe organic phase was then washed with aqueous sodium thiosulfate solution, water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f574fc3e122143dabe90fc1ef8101837
Source dataset
uspto-grants-2008_06
Patent number
US07381728B2

Reaction notes

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