2-Bromopropanoyl chloride → 2-Bromo-N-(3-bromo-2-hydroxyphenyl)propionamide

HRID 598064Notes

Reaction equation

HRID 598064 reaction equation
[Br:1][CH:2]([CH3:6])[C:3](Cl)=[O:4].[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Br:14])[C:9]=1[OH:15].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.O>[Br:1][CH:2]([CH3:6])[C:3]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Br:14])[C:9]=1[OH:15])=[O:4]

Participants

6

Reactant 3

HCID 979802-Bromopropanoyl chlorideHCID 516892Sodium BicarbonateHCID 155315062-Amino-6-bromophenol

Product 1

HCID 672670902-Bromo-N-(3-bromo-2-hydroxyphenyl)propionamideYield 99.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

2-Bromopropionyl chloride (1.47 ml, 14.6 mmol) was added dropwise to a vigorously stirred and ice-cooling mixture of 2-amino-6-bromophenol (2.74 g, 14.6 mmol) and sodium bicarbonate (3.06 g, 36.4 mmol) in ethyl acetate (50 ml)/water (15 ml). The mixture was stirred at 0° C. for 3 h and diluted with water. The aqueous layer was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and concentrated under vacuum. The residue used for the following step without further purification to afford 4.71 g (99%) of the title compound.

Workup

  1. temperatureice-cooling
  2. stirringThe mixture was stirred at 0° C. for 3 h
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue used for the following step without further purification

Sources & evidence

ORD record
ord-f82c6207b6f2421e8092bdd8b66bc246
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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