Benzaldehyde → 3-Bromobenzaldehyde

HRID 2166481Notes

Reaction equation

HRID 2166481 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].ClCl.[CH:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Br:15]Br>ClCCCl>[Br:15][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=1)[CH:7]=[O:14]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 24408BromineHCID 24526ChlorineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 765833-BromobenzaldehydeYield 149.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To 1,2-dichloroethane (1,2-dichloroethane: 143.8 g, 1-bromo-2-chloroethane: 60.5 g, 1,2-dibromoethane: 4.8 g) recovered from Example 2 was added fresh 1,2-dichloroethane (41.5 g), and 98% aluminum chloride (0.65 mol, 88.6 g) was mixed. Into this was blown chlorine (0.25 mol, 17.8 g) at °C., and 97% benzaldehyde (0.50 mol, 54.6 g) was added over 1 hour at 40° C. After bromine (0.30 mol, 48.0 g) was added dropwise to this mixture over 2 hours at 40° C., the resulting mixtures were stirred for 2 hours at that temperature. The post-treatment was carried out by the similar procedure to that in Example 1. As a result, 83.1 g of 3-bromobenzaldehyde were obtained.

Workup

  1. customTo 1,2-dichloroethane (1,2-dichloroethane: 143.8 g, 1-bromo-2-chloroethane: 60.5 g, 1,2-dibromoethane: 4.8 g) recovered from Example 2
  2. additionwas mixed

Sources & evidence

ORD record
ord-9b5e4956ec5e4fb6adeeabc410d3b2fa
Source dataset
uspto-grants-1990_07
Patent number
US04945186

Reaction notes

Loading…