N-bromobutanimide → Benzyl 2-bromo-3-oxobutanoate

HRID 1696863Notes

Reaction equation

HRID 1696863 reaction equation
[C:1]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].C1C(=O)N([Br:22])C(=O)C1.C([O-])(=O)C.[NH4+]>CCOCC>[CH2:8]([O:7][C:1](=[O:6])[CH:2]([Br:22])[C:3](=[O:4])[CH3:5])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 142266Benzyl acetoacetateHCID 517165Ammonium Acetate

Product 1

HCID 10978553Benzyl 2-bromo-3-oxobutanoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirring dispersion of benzyl acetoacetate (20 ml, 116 mmol) and NBS (21.64 g, 122 mmol) in Et2O (1000 ml) was added ammonium acetate (0.893 g, 11.58 mmol). The reaction was stirred at RT for 4 hours and then filtered, washed with water (400 ml), brine, dried over MgSO4 and concentrated in vacuo to give the title compound as a yellow oil; 1H NMR (400 MHz, CDCl3) δ 7.37-7.42 (5H, m, 5×ArH), 5.27 (2H, s, ArCH2OR), 4.82 (1H, s, CHBr), 2.42 (3H, s, RCOCH3).

Workup

  1. filtrationfiltered
  2. washwashed with water (400 ml), brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0734dfea62b54db788700416bba5e415
Source dataset
uspto-grants-2012_04
Patent number
US08163785B2

Reaction notes

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