Methyl 2-(acetylamino)benzoate → Methyl 2-acetamido-5-bromobenzoate

HRID 974413Notes

Reaction equation

HRID 974413 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12](=[O:14])[CH3:13])([O:3][CH3:4])=[O:2].[Br:15]Br>C(O)(=O)C>[C:1]([C:5]1[CH:10]=[C:9]([Br:15])[CH:8]=[CH:7][C:6]=1[NH:11][C:12](=[O:14])[CH3:13])([O:3][CH3:4])=[O:2]

Participants

4

Reactant 2

HCID 17623Methyl 2-(acetylamino)benzoateHCID 24408Bromine

Product 1

HCID 736223Methyl 2-acetamido-5-bromobenzoate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred solution consisting of 14.8 g of N-(2-carbomethoxyphenyl)acetamide and 75 mL of acetic acid was cooled in an ice-acetone bath and 6 mL of bromine were added dropwise. The cooling bath was removed and the solution was stirred for 17 hr. The solution was diluted with 100 mL of methylene chloride and was washed with water. The organic phase was dried over anhydrous sodium sulfate and the solvent was removed in vacuo. The product was purified by elution from a silica gel column with 9:1 methylene chloride: ethyl acetate, which afforded 17.9 g of product as a white solid (m.p. 131°-133° C.). 1H NMR CDCl3) 88.66 (d, 9.0 Hz, 1H), 8.15 (d, 2.0 Hz, 1H), 7.63 (dd, 9.0 Hz, 2.0 Hz, lH), 3.98 (s, 3H, OCH3), 2.27 (s, 3H, COCH3).

Workup

  1. temperaturewas cooled in an ice-acetone bath
  2. customThe cooling bath was removed
  3. additionThe solution was diluted with 100 mL of methylene chloride
  4. washwas washed with water
  5. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  6. customthe solvent was removed in vacuo
  7. customThe product was purified by elution from a silica gel column with 9:1 methylene chloride

Sources & evidence

ORD record
ord-75c7ff10fa4949a399d6247b7b819d69
Source dataset
uspto-grants-1991_11
Patent number
US05068392

Reaction notes

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