Dimethylformamide → 2-Bromo-4-methylbenzamide

HRID 662019

Reaction equation

HRID 662019 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C[N:13](C=O)C>C1(C)C=CC=CC=1.S(Cl)(Cl)=O>[Br:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:13])=[O:5]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 2262922-Bromo-4-methylbenzoic acid

Product 1

HCID 2623402-Bromo-4-methylbenzamideYield 99%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 2-bromo-4-methylbenzoic acid (15.0 g, 69.8 mmol) in toluene (60 mL), thionyl chloride (10.3 mL) and DMF (0.10 mL) were added and stirred at 50° C. for 3 h. After cooling to room temperature, the excess thionyl chloride was removed in vacuo. The residue was dissolved in toluene (50 mL), and the mixture was added to the solution of ammonia (25%, 60 mL). The white precipitate was filtered over Celite and dried in vacuo to afford 2-bromo-4-methylbenzamide (14.8 g, 99%).

Workup

  1. additionwere added
  2. temperatureAfter cooling 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 the solution of ammonia (25%, 60 mL)
  6. filtrationThe white precipitate was filtered over Celite
  7. customdried in vacuo

Sources & evidence

ORD record
ord-5368abd18b004492846f479fd4b79fd8
Source dataset
uspto-grants-2011_12
Patent number
US08084449B2

Linked notes

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