Dimethylformamide → 3-Bromo-5-methoxybenzamide

HRID 657333Notes

Reaction equation

HRID 657333 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) were added thionyl chloride (9.89 g, 83.1 mmol) and DMF (0.10 mL) and the mixture stirred at 50° C. for 4 h. The mixture was allowed to cool 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. temperatureto cool to room temperature
  2. customthe excess thionyl chloride was removed in vacuo
  3. dissolutionThe residue was dissolved in toluene (50 mL)
  4. additionthe mixture was added to a solution of ammonia (25%, 50 mL)
  5. customA precipitate formed
  6. filtrationwas filtered off
  7. customdried

Sources & evidence

ORD record
ord-46d8c9eb00de4d58aeb7ebedbe9e5b1d
Source dataset
uspto-grants-2011_12
Patent number
US08071588B2

Reaction notes

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