Water → 5-Bromo-4-chlorothiophene-2-carboxylic acid
Reaction equation
[OH-:1].[Na+].O.BrBr.[Br:6][C:7]1[S:11][C:10]([C:12](=[O:14])C)=[CH:9][C:8]=1[Cl:15]>O1CCOCC1>[Br:6][C:7]1[S:11][C:10]([C:12]([OH:14])=[O:1])=[CH:9][C:8]=1[Cl:15]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Sodium hydroxide (50% in water) (5.82 ml, 110 mmol) was added to water (15 ml), and the mixture was chilled to 0° C. Bromine solution (1.669 ml, 32.6 mmol) was added, followed by dropwise addition of a solution of 1-(5-bromo-4-chlorothiophen-2-yl)ethanone (2.4 g, 10.02 mmol) in dioxane (18 ml). The mixture was stirred for 1.5 hours at room temperature, washed with dichloromethane, and then the aqueous phase was adjusted to pH 1 using 4N aqueous HCl. The precipitated solid was collected by filtration to give the title compound.
Workup
- washwashed with dichloromethane
- filtrationThe precipitated solid was collected by filtration
Sources & evidence
- ORD record
- ord-4e30daf8ad744cd0b8f43dcc148a2abc
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193723B2
Reaction notes
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