2-Bromobenzaldehyde → Methyl 2-azido-3-(2-bromophenyl)prop-2-enoate

HRID 1384814Notes

Reaction equation

HRID 1384814 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[N:10]([CH2:13][C:14]([O:16][CH3:17])=[O:15])=[N+:11]=[N-:12].C[O-].[Na+]>CO>[N:10]([C:13](=[CH:4][C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[Br:1])[C:14]([O:16][CH3:17])=[O:15])=[N+:11]=[N-:12]

Participants

5

Reactant 3

HCID 811292-BromobenzaldehydeHCID 4020482Methyl 2-azidoacetateHCID 10942334Sodium Methoxide

Product 1

HCID 78114796Methyl 2-azido-3-(2-bromophenyl)prop-2-enoateYield 18,636.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 75 ml (624 mmol) of 2-bromobenzaldehyde and of 252 g (2.2 mmol) of methyl azidoacetate in 160 ml of methanol is added dropwise over 3 h, at a temperature of −10 to −8° C., under nitrogen and with mechanical stirring, to a solution of 476 ml of sodium methoxide (30% in methanol) in 950 ml of methanol. Stirring is maintained for 2 h at a temperature below 5° C. The mixture is poured onto 1.5 kg of ice. The precipitate is collected by filtration, washed with water and dried under reduced pressure with light excluded. 116 g (0.41 mol) of solid are obtained, which solid is used quickly in the following stage.

Workup

  1. temperatureis maintained for 2 h at a temperature below 5° C
  2. filtrationThe precipitate is collected by filtration
  3. washwashed with water
  4. customdried under reduced pressure with light

Sources & evidence

ORD record
ord-bb157df2936341a7a8e25fe28bf829fa
Source dataset
uspto-grants-2001_07
Patent number
US06262045B1

Reaction notes

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