Hydrogen Bromide → Methyl 3-bromo-2-chlorobenzoate
Reaction equation
N[C:2]1[C:3]([Cl:12])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].N([O-])=O.[Na+].[BrH:17]>O.[Cu]Br>[Br:17][C:2]1[C:3]([Cl:12])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of methyl 3-amino-2-chlorobenzoate (2.0 g, 11 mmol) in 48% HBr (10 mL) and water (20 mL) was added an aqueous solution of sodium nitrite (0.89 g, 13 mmol) at 0° C. The mixture was allowed to stir at 0° C. for 30 minutes before it was added into a suspension of copper(I) bromide (2.3 g, 16 mmol) in water (10 mL) and 48% HBr (5 mL) at 0° C. The reaction was allowed to warm to RT slowly, and then heated to 60° C. for 5 minutes. The product was extracted with DCM (100 mL X 2). The extractions were combined, dried over sodium sulfate, adsorbed onto silica gel, and purified by MPLC to provide methyl 3-bromo-2-chlorobenzoate. LC-MS (IE, m/z): 251 [M+1]+
Workup
- temperatureto warm to RT slowly
- temperatureheated to 60° C. for 5 minutes
- extractionThe product was extracted with DCM (100 mL X 2)
- extractionThe extractions
- dry with materialdried over sodium sulfate
- custompurified by MPLC
Sources & evidence
- ORD record
- ord-e16ba76857c040d889c088d21f972569
- Source dataset
- uspto-grants-2015_04
- Patent number
- US08999990B2
Reaction notes
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