Water → 1-(2-Amino-5-bromophenyl)ethan-1-one

HRID 1255815Notes

Reaction equation

HRID 1255815 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.OS(O)(=O)=O.O>ClCCl>[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

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 110862'-AminoacetophenoneHCID 67184N-bromobutanimide

Product 1

HCID 110747461-(2-Amino-5-bromophenyl)ethan-1-oneYield 58.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 1-(2-aminophenyl)ethanone (5.0 g, 0.037 mol) in dichloromethane (60 mL) was added NBS (7.3 g, 0.04 mol). The resulting mixture was cooled to 0° C. followed by the addition of H2SO4 (0.05 mL). It was allowed to warm to room temperature and stirred overnight. To the reaction mixture was added water and extracted with dichloromethane, dried over MgSO4. The crude product was purified by column chromatography eluted with ethyl acetate/hexanes to afford the titled compound (4.6 g, 58%) as a yellow solid. m.p 87-89° C. 1H NMR (400 MHz, CDCl3): δ 2.56 (s, 3H), 6.31 (s, 2H), 7.56 (d, J=8.8 Hz, 1H), 7.33 (dd, J=2.4 Hz, 1H), 7.80 (d, J=2.4 Hz, 1H).

Workup

  1. temperatureto warm to room temperature
  2. extractionextracted with dichloromethane
  3. dry with materialdried over MgSO4
  4. customThe crude product was purified by column chromatography
  5. washeluted with ethyl acetate/hexanes

Sources & evidence

ORD record
ord-8fc14d3d49be49d6af880c131944b13c
Source dataset
uspto-grants-2013_06
Patent number
US08461157B2

Reaction notes

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