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

HRID 2175220Notes

Reaction equation

HRID 2175220 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[OH:9].C(=O)(O)[O-].[Na+].[Br:15][CH:16]([CH3:20])[C:17](Cl)=[O:18]>C(OCC)(=O)C.O>[Br:15][CH:16]([CH3:20])[C:17]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[OH:9])=[O:18]

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 91.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 2-amino-6-bromophenol (3 g, 15.96 mmol) and sodium bicarbonate (3.35 g, 39.9 mmol) in ethyl acetate (30 mL) and water (10 mL) at 0° C. was added 2-bromopropionyl chloride (1.61 ml, 15.96 mmol) dropwise. The reaction mixture was stirred at 0° C. for 3 h and then diluted with water. The resulting mixture was extracted with EtOAc and the organic layer was washed with brine, dried over anhydrous MgSO4, filtered, and concentrated to afford the title compound (4.7 g, 73% yield). LCMS, [M+H]+=323.8.

Workup

  1. extractionThe resulting mixture was extracted with EtOAc
  2. washthe organic layer was washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a7b041572e6141ab8f60de57255df68b
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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