Bromine → N-benzyl-4-bromo-3-oxobutanamide

HRID 526717

Reaction equation

HRID 526717 reaction equation
[CH2:1]([NH:8][C:9](=[O:14])[CH2:10][C:11](=[O:13])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:15]Br.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([NH:8][C:9](=[O:14])[CH2:10][C:11](=[O:13])[CH2:12][Br:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24408Bromine2×HCID 70159Acetoacetobenzylamide2×HCID 516892Sodium Bicarbonate

Product 1

HCID 71502812N-benzyl-4-bromo-3-oxobutanamideYield 80.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22.5 °C

Procedure

To a solution of N-benzyl-3-oxobutanamide (compound A 100 g, 522.9 mmol) in dichloromethane (500 ml) at 0-5° C. was added dropwise a solution of bromine (25.55 ml, 575.2 mmol) over 6 h. The reaction mixture was warmed up to 20-25° C. and stirred for 2 hours (bromine colour disappeared). An aqueous solution (600 mL) of sodium bicarbonate (65.9 g, 784.44 mmol) was added to the mixture. The organic layer was separated, washed with brine (200 mL), and then evaporated to dryness to give N-benzyl-4-bromo-3-oxobutanamide (114.25 g, quantitative) and was used in the next step without further purification.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine (200 mL)
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-c45d61462981459f9eec528879b2551d
Source dataset
uspto-grants-2016_05
Patent number
US09346751B2

Linked notes

Loading…