Ammonia → 2-(4-Bromophenyl)acetamide

HRID 220558Notes

Reaction equation

HRID 220558 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](Cl)=[O:10])=[CH:4][CH:3]=1.[NH3:12]>O1CCOCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH2:12])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 181552Benzeneacetyl chloride, 4-bromo-

Product 1

HCID 2569512-(4-Bromophenyl)acetamideYield 109%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Add 2-(4-bromo-phenyl)-acetyl chloride (1.00 g, 4.28 mmol) to a solution of ammonia in dioxane (0.5 M, 15 mL) at room temperature. Stir for 30 min., then quench with water. Extract with DCM (10 mL) and pass through an IST Phase Separator Frit® and concentrate until precipitate appears. Collect precipitate by filtration, wash powder with DCM, then dissolve in methanol, filter and concentrate to give a white powder (1.0 g, 109%). 1H-NMR (300 MHz, MeOD) δ 7.48 (d, 2H), 7.25 (d, 2H), 3.50 (s, 2H).

Workup

  1. customquench with water
  2. extractionExtract with DCM (10 mL)
  3. concentrationconcentrate until precipitate appears
  4. customCollect precipitate
  5. filtrationby filtration
  6. washwash powder with DCM
  7. dissolutiondissolve in methanol
  8. filtrationfilter
  9. concentrationconcentrate

Sources & evidence

ORD record
ord-5f5c8f17f87b4bcaa9f0147ff74c86cf
Source dataset
uspto-grants-2012_06
Patent number
US08202873B2

Reaction notes

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