N-bromobutanimide → 2-Amino-5-bromobenzophenone

HRID 1497698Notes

Reaction equation

HRID 1497698 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9].C1C(=O)N([Br:23])C(=O)C1>C(Cl)Cl>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:23])=[CH:4][C:3]=1[C:8]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:9]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 760802-Aminobenzophenone

Product 1

HCID 996772-Amino-5-bromobenzophenoneYield 91.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a solution of (2-Amino-phenyl)-phenyl-methanone (5 g, 25 mmol) in DCM (100 mL) is cooled to −10° C., then NBS (4.512 g, 25 mmol) is added in 30 minutes. After the addition the mixture is stirred at −10° C. for 2 h. The mixture is diluted with DCM, washed with salt NaHCO3 (2×100 mL), salt NaCl (100 mL), dried over anhydrous Na2SO4, filtered and concentrated to give product (6.3 g), which is used for the next step without further purification.

Workup

  1. additionAfter the addition the mixture
  2. washwashed with salt NaHCO3 (2×100 mL), salt NaCl (100 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9a7ad94610664da8a891acb3e777865b
Source dataset
uspto-grants-2015_12
Patent number
US09199988B2

Reaction notes

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