2,5-Dibromobenzoic acid → 2,5-Dibromobenzoyl chloride

HRID 458488Notes

Reaction equation

HRID 458488 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:14])=O>>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([Cl:14])=[O:5]

Participants

3

Reactant 2

HCID 118912,5-Dibromobenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 134505242,5-Dibromobenzoyl chlorideYield 75.1%

Procedure

Into a 2 L flask fitted with a reflux condenser and magnetic stir-bar was introduced 2,5-dibromobenzoic acid (50.0 g, 0.1786 mol) and thionyl chloride (150 mL, 2.04 mol). The mixture was refluxed for 8 hours. Most of the thionyl chloride was distilled off followed by removal of the remainder by rotary evaporation. Distillation gave 40 g of 2,5-dibromobenzoyl chloride. (pot temperature 110° C.; distillation temp 70° C./0.70 mm Hg).

Workup

  1. customInto a 2 L flask fitted with a reflux condenser and magnetic stir-bar
  2. temperatureThe mixture was refluxed for 8 hours
  3. distillationMost of the thionyl chloride was distilled off
  4. customfollowed by removal of the remainder by rotary evaporation
  5. distillationDistillation

Sources & evidence

ORD record
ord-012b5e650d8b46feae17d2ac4039befd
Source dataset
uspto-grants-2007_03
Patent number
US07192657B2

Reaction notes

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