Dimethylformamide → 3-Bromo-5-methoxybenzamide

HRID 564453Notes

Reaction equation

HRID 564453 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[C:5](O)=[O:6].S(Cl)(Cl)=O.C[N:18](C=O)C>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[C:5]([NH2:18])=[O:6]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 40600483-Bromo-5-methoxybenzoic acid

Product 1

HCID 578133713-Bromo-5-methoxybenzamideYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 3-bromo-5-(methyloxy)benzoic acid (9.6 g, 41.6 mmol) in toluene (60 mL), thionyl chloride (9.89 g, 83.1 mmol) and DMF (0.10 mL) were added and stirred at 50° C. for 4 h. The reaction was allowed to cooled to room temperature, and then the excess thionyl chloride was removed in vacuo. The residue was dissolved in toluene (50 mL) and the mixture was added to a solution of ammonia (25%, 50 mL). A precipitate formed and was filtered off using Celite, and dried, to afford 3-bromo-5-(methyloxy)benzamide (8.70 g, 90%).

Workup

  1. additionwere added
  2. temperatureto cooled to room temperature
  3. customthe excess thionyl chloride was removed in vacuo
  4. dissolutionThe residue was dissolved in toluene (50 mL)
  5. additionthe mixture was added to a solution of ammonia (25%, 50 mL)
  6. customA precipitate formed
  7. filtrationwas filtered off
  8. customdried

Sources & evidence

ORD record
ord-b4ee4110bc1b46b2870b05b8217fa091
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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