2'-Aminoacetophenone → 1-(2-Amino-5-bromophenyl)ethan-1-one

HRID 1625708Notes

Reaction equation

HRID 1625708 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].C1C(=O)N([Br:18])C(=O)C1>C(Cl)Cl>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:18])=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 110862'-AminoacetophenoneHCID 67184N-bromobutanimide

Product 1

HCID 110747461-(2-Amino-5-bromophenyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

A flask charged with 1-(2-aminophenyl)ethanone (135 mg) and DCM (2.5 mL) was cooled to −10° C. and NBS (178 mg) was added in several portions over 30 min. The reaction mixture was diluted with 10 mL DCM, washed with sat. aqueous NaHCO3, dried over Na2SO4, filtered and concentrated under reduced pressure, affording the title compound. MS (ESI+): m/z 215.06 (MH+). 1H NMR (400 MHz, CDCl3): δ 7.79 (s, 1H), 7.31 (d, J=8.8 Hz, 1H), 6.54 (d, J=8.8 Hz, 1H), 6.30 (br, 2H), 2.55 (s, 3H).

Workup

  1. washwashed with sat. aqueous NaHCO3
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fd67351b5bdc45bcaffb36285ab5fceb
Source dataset
uspto-grants-2014_07
Patent number
US08785151B2

Reaction notes

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