Water → 5-Bromo-2,4-dichlorobenzoic acid

HRID 46225

Reaction equation

HRID 46225 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Br:12]Br.O>ClS(O)(=O)=O.[S]>[Br:12][C:8]1[C:9]([Cl:11])=[CH:10][C:2]([Cl:1])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]

Participants

6

Reactant 3

HCID 962WaterHCID 57872,4-Dichlorobenzoic Acid2×HCID 24408Bromine

Product 1

HCID 218625655-Bromo-2,4-dichlorobenzoic acidYield 187.5%

Reagents, catalysts & solvents 2

HCID 5362487SulfurCatalystHCID 24638Chlorosulfonic acidSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2,4-dichlorobenzoic acid (compound 80, 25.0 g, 131 mmol) in chlorosulfonic acid (100 mL) was added bromine (3.4 mL, 65 mmol) and sulfur (0.20 g, 6.6 mmol). The reaction mixture was stirred at 70° C. overnight and then cooled to ambient temperature. The reaction mixture was poured into iced water. The resulting solid was isolated by filtration and dried in vacuo to yield title compound (32.9 g, 93%) as pale brown solid.

Workup

  1. temperaturecooled to ambient temperature
  2. customThe resulting solid was isolated by filtration
  3. customdried in vacuo

Sources & evidence

ORD record
ord-541340427c5d4696b208240ea8e76d24
Source dataset
uspto-grants-2013_09
Patent number
US08541380B2

Linked notes

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