Phosphorus tribromide → 2-(Bromomethyl)-1-methoxy-3-methylbenzene
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[CH2:10]O.P(Br)(Br)[Br:13].C(=O)(O)[O-].[Na+]>ClCCl>[Br:13][CH2:10][C:3]1[C:4]([O:8][CH3:9])=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
[2-Methyl-6-(methyloxy)phenyl]methanol (for a preparation see Intermediate 56)(300 mg, 1.971 mmol) in dichloromethane (4.5 ml) under nitrogen was stirred and cooled to −10° C. A solution of phosphorus tribromide (186 μl, 1.97 mmol) in DCM (4 ml) was then added dropwise over about 15 min and the solution stirred for a further 30 min at this temperature. The solution was allowed to warm up to ambient temperature. After a few hours, saturated aqueous sodium bicarbonate (approximately 5 ml) was added and the mixture stirred vigorously. The suspension was stored in freezer overnight. The phases were separated and the aqueous phase extracted further with chloroform. The combined organic extracts were dried (MgSO4), filtered and evaporated in vacuo to give the title compound as yellow solid (424 mg); LCMS: (System 4) No MH+, tRET=3.01 min.
Workup
- stirringthe solution stirred for a further 30 min at this temperature
- temperatureto warm up to ambient temperature
- waitAfter a few hours
- stirringthe mixture stirred vigorously
- customThe phases were separated
- extractionthe aqueous phase extracted further with chloroform
- dry with materialThe combined organic extracts were dried (MgSO4)
- filtrationfiltered
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-59749fe2c4ac4015a77820dc9c889766
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399436B2
Reaction notes
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