Benzaldehyde → 3-Bromobenzaldehyde

HRID 2166479Notes

Reaction equation

HRID 2166479 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH:5](=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Br:13]Br>ClCCCl>[Br:13][C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=1)[CH:5]=[O:12]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 24408BromineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 765833-BromobenzaldehydeYield 90.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of 1,2-dichloroethane (250 g) with 98% aluminum chloride (0.65 mol, 88.6 g) was added 97% benzaldehyde (0.50 mol, 54.6 g) over 1 hour at 40° C. After bromine (0.55 mol, 88.0 g) was added over 2 hours at 40° C., this mixture was stirred for 2 hours at the same temperature. After the reaction mixture being added to ice water (375.0 g) and stirred thoroughly, this was allowed to stand and separated. The organic phase was washed with 100 ml of water, further with 100 ml of 0.5% aqueous solution of sodium carbonate, and finally with 100 ml of water. Then, 241.0 g of solvent were recovered and the residue was distilled, obtaining 83.5 g of 3-bromobenzaldehyde.

Workup

  1. stirringstirred thoroughly
  2. customseparated
  3. washThe organic phase was washed with 100 ml of water, further with 100 ml of 0.5% aqueous solution of sodium carbonate
  4. customThen, 241.0 g of solvent were recovered
  5. distillationthe residue was distilled

Sources & evidence

ORD record
ord-7de891eca9294476aad9d250ac3ac85f
Source dataset
uspto-grants-1990_07
Patent number
US04945186

Reaction notes

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