3-Bromo-4-methoxybenzaldehyde → Methyl 3-bromo-4-methoxy-alpha-azidocinnamate

HRID 2395768Notes

Reaction equation

HRID 2395768 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=O.[N:12]([CH2:15][C:16]([O:18][CH3:19])=[O:17])=[N+:13]=[N-:14]>>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[C:15]([N:12]=[N+:13]=[N-:14])[C:16]([O:18][CH3:19])=[O:17]

Participants

3

Reactant 2

HCID 986623-Bromo-4-methoxybenzaldehydeHCID 4020482Methyl 2-azidoacetate

Product 1

HCID 53891859Methyl 3-bromo-4-methoxy-alpha-azidocinnamate

Procedure

Following the general procedure of PREPARATION 61 and making non-critical variations but starting with 3-bromo-4-methoxybenzaldehyde (5.0 g) and methyl azidoacetate (10.7 g), the title compound is obtained, NMR (300 MHz, CDCl3) 8.10, 7.73, 6.89, 6.79, 3.94 and 3.90 δ.

Workup

  1. customthe general procedure of PREPARATION 61

Sources & evidence

ORD record
ord-a3550366f6244ad6a8e36db0a3736886
Source dataset
uspto-grants-1996_02
Patent number
US05489593

Reaction notes

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