Water → 4-(bromomethyl)benzamide

HRID 1506147Notes

Reaction equation

HRID 1506147 reaction equation
[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[CH:5][CH:4]=1.S(Cl)(Cl)=O.[NH4+:16].[OH-].O>C(OCC)(=O)C>[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:16])=[O:8])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 225994-(Bromomethyl)benzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 5842164-(bromomethyl)benzamideYield 91.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-(Bromomethyl)benzoic acid (300 mg, 1.40 mmol) in ethyl acetate (5 mL) was stirred with thionyl chloride (249 μL, 3.50 mmol) at 75° C. for 9 hours. The reaction mixture was allowed to cool to room temperature and concentrated under reduced pressure. The residue was dissolved in dichloromethane (5 mL) and stirred with 28% ammonia aqueous solution (380 μL, 5.60 mmol) under cooling with ice for 80 minutes. The reaction mixture was mixed with water, and the precipitate was collected by filtration, washed with dichloromethane to give the title compound as a colorless solid (274 mg, yield 91%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane (5 mL)
  3. temperatureunder cooling with ice for 80 minutes
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with dichloromethane

Sources & evidence

ORD record
ord-9efc8cee6eeb4cec80e0230262ce5ec0
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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