Toluene → Ethyl 2-bromo-4-chlorobenzoate
Reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[C:16]1(C)C=CC=C[CH:17]=1>>[Br:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:16][CH3:17])=[O:5]Participants
4
Conditions
- Temperature
- 90 °C
Procedure
A mixture of 2-bromo-4-chlorobenzoic acid (235 mg, 1 mmol) and thionyl chloride (238 mg, 146 ul, 2 mmol) in toluene (5 ml) was heated at 90° C. for 1 hour. The reaction mixture was cooled and the solvent evaporated. The residue was dissolved in THF (1 ml) and treated with ethanol (1 ml). The solution was evaporated to dryness leaving the title compound as a yellow oil 263 mg 100%
Workup
- temperatureThe reaction mixture was cooled
- customthe solvent evaporated
- dissolutionThe residue was dissolved in THF (1 ml)
- additiontreated with ethanol (1 ml)
- customThe solution was evaporated to dryness
Sources & evidence
- ORD record
- ord-aa690f5f5a4c44bd9a72bf9efae9419f
- Source dataset
- uspto-grants-2008_11
- Patent number
- US07446222B2
Reaction notes
Loading…