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

HRID 1399942Notes

Reaction equation

HRID 1399942 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-9a83b1182d4641afa7d64ec1c9255264
Source dataset
uspto-grants-2014_12
Patent number
US08906909B2

Reaction notes

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