Boron tribromide → 2,6-Dichloro-4-hydroxybenzoic acid
Reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([O:11]C)[CH:8]=[C:7]([Cl:13])[C:3]=1[C:4]([OH:6])=[O:5].B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]([Cl:13])[C:3]=1[C:4]([OH:6])=[O:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
2,6-Dichloro-4-methoxy-benzoic acid (500 mg, 2.3 mmol) was taken up in CH2Cl2 and cooled to −78° C. BBr3 (6.9 ml of a 1 M solution in CH2Cl2) was added to the solution at −78° C. The solution was warmed to 25° C. and stirred at that temperature for 16 h. The solution was quenched with 3 N NaOH. The aqueous layer was extracted with CH2CO2. The aqueous layer was cooled (0° C.) and acidified with conc. HCl (pH=1-2). The aqueous layer was extracted with CH2Cl2. The combined organic layers were dried (Na2SO4). Filtration and concentration gave the crude phenol which was used without further purification.
Workup
- temperatureThe solution was warmed to 25° C.
- customThe solution was quenched with 3 N NaOH
- extractionThe aqueous layer was extracted with CH2CO2
- temperatureThe aqueous layer was cooled (0° C.)
- extractionThe aqueous layer was extracted with CH2Cl2
- dry with materialThe combined organic layers were dried (Na2SO4)
- filtrationFiltration and concentration
Sources & evidence
- ORD record
- ord-963a4de15ac24a229f16311e9d0a4070
- Source dataset
- uspto-grants-2004_02
- Patent number
- US06689765B2
Reaction notes
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