Bromine → Methyl 5-bromo-2-hydroxy-4-methylbenzoate
Reaction equation
[Br:1]Br.[OH:3][C:4]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]>C(Cl)(Cl)Cl>[Br:1][C:11]1[C:12]([CH3:14])=[CH:13][C:4]([OH:3])=[C:5]([CH:10]=1)[C:6]([O:8][CH3:9])=[O:7]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Bromine (0.47 ml, 9.03 mmol) was added dropwise to a solution of methyl 2-hydroxy-4-methylbenzoate (may be prepared as described in Description 1; 1.5 g, 9.03 mmol) in chloroform (20 ml) at 0° C. The solution was stirred for 1 hour at 0° C. The reaction was quenched with saturated sodium sulphite (10 ml), then extracted with dichloromethane (2×10 ml). The combined organic layers were washed with brine (10 ml), dried (MgSO4) and the solvent removed in vacuo to yield the title compound as a white solid. 2.24 g.
Workup
- customThe reaction was quenched with saturated sodium sulphite (10 ml)
- extractionextracted with dichloromethane (2×10 ml)
- washThe combined organic layers were washed with brine (10 ml)
- dry with materialdried (MgSO4)
- customthe solvent removed in vacuo
Sources & evidence
- ORD record
- ord-6ae8919572dd4e8cac11cd3bb008f121
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365551B2
Reaction notes
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