Hydrogen Bromide → 4'-Bromo-2'-phenylacetanilide

HRID 1518630Notes

Reaction equation

HRID 1518630 reaction equation
[C:1]1([C:7]2[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=2[NH:9][C:10](=[O:12])[CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BrH:17]>C(O)(=O)C.C(Cl)(Cl)(Cl)Cl>[C:1]1([C:7]2[CH:16]=[C:15]([Br:17])[CH:14]=[CH:13][C:8]=2[NH:9][C:10](=[O:12])[CH3:11])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 164472-Acetamidobiphenyl

Product 1

HCID 2424004'-Bromo-2'-phenylacetanilideYield 91.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

2-Phenyl-N-acetylaniline (6.21 g, 29.40 mmol) was dissolved in acetic acid (70 mL). Thereto was dropwise added under ice bath a separately prepared solution of hydrogen bromide (6.14 g, 38.42 mmol) dissolved in carbon tetrachloride (19.21 mL) and the mixture was stirred at room temperature overnight. The solution was concentrated under reduced pressure, to the residue was added water (20 mL) and subsequently ethanol (30 mL), and the mixture was stirred under ice bath for 1 hour. The precipitate was collected by filtration, washed with ethanol/water (=1:1), dried under reduced pressure to obtain 2-phenyl-4-bromo-N-acetylaniline (7.79 g).

Workup

  1. concentrationThe solution was concentrated under reduced pressure, to the residue
  2. additionwas added water (20 mL) and subsequently ethanol (30 mL)
  3. stirringthe mixture was stirred under ice bath for 1 hour
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with ethanol/water (=1:1)
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-c1a270181535486187596470ab6be54a
Source dataset
uspto-grants-2015_07
Patent number
US09072734B2

Reaction notes

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