Bromoacetyl bromide → 2-bromo-N-(2-chloro-5-cyano-3-nitrophenyl)acetamide

HRID 921870Notes

Reaction equation

HRID 921870 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[Cl:10])[C:5]#[N:6].[Br:14][CH2:15][C:16](Br)=[O:17]>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[Br:14][CH2:15][C:16]([NH:1][C:2]1[CH:3]=[C:4]([C:5]#[N:6])[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[Cl:10])=[O:17]

Participants

5

Reactant 2

HCID 61147Bromoacetyl bromideHCID 717559993-Amino-4-chloro-5-nitrobenzonitrile

Product 1

HCID 899223412-bromo-N-(2-chloro-5-cyano-3-nitrophenyl)acetamideYield 82.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

To the solution of 3-amino-4-chloro-5-nitrobenzonitrile (300 mg, 1.518 mmol) in DCM (12 mL) at 0° C. was added TEA (0.635 mL, 4.56 mmol) and then 2-bromoacetyl bromide (0.291 mL, 3.34 mmol) was added drop wise. The reaction mixture was stirred at 0° C. for 1 h. LC-MS indicated a new peak. Then it was diluted with DCM and saturated aqueous sodium bicarbonate solution was added. After separating the layers, the aqueous layer was further extracted with DCM. The combined organic extracts were washed with water, brine, dried over MgSO4, filtered and concentrated. Purification via flash chromatography (0-70% EtOAc in DCM, 40 g) gave 2-bromo-N-(2-chloro-5-cyano-3-nitrophenyl)acetamide (400 mg) as a light yellow solid.

Workup

  1. additionwas added
  2. customAfter separating the layers
  3. extractionthe aqueous layer was further extracted with DCM
  4. washThe combined organic extracts were washed with water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification via flash chromatography (0-70% EtOAc in DCM, 40 g)

Sources & evidence

ORD record
ord-15d7fda8e4554376b6d878bf2682ebd2
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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