Thionyl Chloride → 5-Bromo-2,4-dimethoxybenzoyl chloride
Reaction equation
[Br:1][C:2]1[C:3]([O:13][CH3:14])=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7](O)=[O:8].S(Cl)([Cl:17])=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:3]([O:13][CH3:14])=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([Cl:17])=[O:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
Under a nitrogen atmosphere, 5-bromo-2,4-dimethoxybenzoic acid (40.0 g) was suspended in toluene solution (DMF concentration: 300 ppm, 200 mL). To the suspension was added dropwise thionyl chloride (21.9 g) at 75° C. After stirring at 75° C. for 1 hr, completion of the reaction was confirmed by HPLC. Toluene and excess thionyl chloride were evaporated under reduced pressure. Toluene (100 mL) was added to the concentrated residue, and the mixture was concentrated again under reduced pressure. THF (100 mL) was added to the obtained 5-bromo-2,4-dimethoxybenzoic acid chloride, which was directly used in the next step.
Workup
- customToluene and excess thionyl chloride were evaporated under reduced pressure
- additionToluene (100 mL) was added to the concentrated residue
- concentrationthe mixture was concentrated again under reduced pressure
- additionTHF (100 mL) was added to the obtained 5-bromo-2,4-dimethoxybenzoic acid chloride, which
Sources & evidence
- ORD record
- ord-e0e3d20ee74a4a729e4c0e64db93c569
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08420821B2
Reaction notes
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