Methanol → Methyl 2-bromo-3-chlorobenzoate
Reaction equation
[Br:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:16]O>C(Cl)Cl.CN(C=O)C>[CH3:16][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[C:10]([Cl:11])[C:2]=1[Br:1]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 2-bromo-3-chlorobenzoic acid (7.29 mmol) in 20 mL DCM and 1 mL DMF was added 1.06 mL thionyl chloride. After stirring at RT overnight, 5 mL MeOH were added and stirring was continued at RT for 1 h. The reaction mixture was cooled in an ice bath, quenched by adding a sat. aq. NaHCO3 solution and extracted twice with DCM. The combined organic layers were dried over MgSO4 and concentrated in vacuo to give the desired product as colorless oil.
Workup
- stirringstirring
- waitwas continued at RT for 1 h
- temperatureThe reaction mixture was cooled in an ice bath
- customquenched
- additionby adding a sat. aq. NaHCO3 solution
- extractionextracted twice with DCM
- dry with materialThe combined organic layers were dried over MgSO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-7abd6da93a9942c59eeb9ef8012602fc
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409917B2
Reaction notes
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