Chlorine → 5-Bromo-3-chloro-2-hydroxybenzaldehyde

HRID 1871067Notes

Reaction equation

HRID 1871067 reaction equation
[Br:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.[Cl:11]Cl>C(O)(=O)C>[Cl:11][C:4]1[CH:3]=[C:2]([Br:1])[CH:9]=[C:6]([CH:7]=[O:8])[C:5]=1[OH:10]

Participants

4

Reactant 2

HCID 24526Chlorine2×HCID 728635-Bromosalicylaldehyde

Product 1

HCID 27166965-Bromo-3-chloro-2-hydroxybenzaldehydeYield 82%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a 5 L round bottom flask fitted with a mechanical stirrer and gas addition tube was added 5-bromosalicylaldehyde (495 g, 2.46 mol) and to acetic acid at ambient temperature to form a slurry. To this mixture was added chlorine gas at a moderate rate until a slight molar excess of chlorine (183 g, 1.05 mol) had dissolved. After the addition was stopped the reaction allowed to proceed overnight. The solid formed was recovered by filtration and the filtrate diluted into water (2.5 L). The mixture was stirred vigorously for 20 minutes, the product collected by filtration and washed with water. The combined solids were vacuum dried to give the desired 3-chloro-5-bromosalicylaldehyde (475 g, 82% yield).

Workup

  1. customTo a 5 L round bottom flask fitted with a mechanical stirrer and gas addition tube
  2. dissolutionhad dissolved
  3. additionAfter the addition
  4. customThe solid formed
  5. filtrationwas recovered by filtration
  6. additionthe filtrate diluted into water (2.5 L)
  7. filtrationthe product collected by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-39c03d6facb94a2f8a6200eab80c17e2
Source dataset
uspto-grants-2000_08
Patent number
US06100423

Reaction notes

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