Dimethylformamide → 2-Bromo-4-methylbenzamide

HRID 657317

Reaction equation

HRID 657317 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-46a2cb238e6d4baca3a6f85a64244329
Source dataset
uspto-grants-2011_12
Patent number
US08071588B2

Linked notes

Loading…