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

HRID 864414Notes

Reaction equation

HRID 864414 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-b98a232a177f444c9ad37bff1f1ef05f
Source dataset
uspto-grants-1996_10
Patent number
US05563142

Reaction notes

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