Azobisisobutyronitrile → (R)-3-(4-bromo-3-(bromomethyl)-5-methylphenoxy)tetrahydrofuran
Reaction equation
[Br:1][C:2]1[C:13]([CH3:14])=[CH:12][C:5]([O:6][C@@H:7]2[CH2:11][CH2:10][O:9][CH2:8]2)=[CH:4][C:3]=1[CH3:15].[Br:16]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[C:13]([CH3:14])=[CH:12][C:5]([O:6][C@@H:7]2[CH2:11][CH2:10][O:9][CH2:8]2)=[CH:4][C:3]=1[CH2:15][Br:16]Participants
Conditions
- Temperature
- 60 °C
Procedure
(R)-3-(4-Bromo-3,5-dimethylphenoxy)tetrahydrofuran 35a (2.27 g, 8.37 mmol), N-bromosuccinimide (1.79 g, 10.04 mmol) and azobisisobutyronitrile (64 mg, 0.42 mmol) were dissolved in 50 mL of carbon tetrachloride. The reaction solution was heated to 60° C. and stirred for 12 hours. The resulting solution was concentrated under reduced pressure, mixed with 50 mL of tert-butyl methyl ether, stirred for 10 minutes, filtered and washed with tert-butyl methyl ether (20 mL×2). The combined filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography with elution system B to obtain the title compound (R)-3-(4-bromo-3-(bromomethyl)-5-methylphenoxy)tetrahydrofuran 35b (707 mg, yield 24.2%) as a light yellow solid.
Workup
- concentrationThe resulting solution was concentrated under reduced pressure
- additionmixed with 50 mL of tert-butyl methyl ether
- stirringstirred for 10 minutes
- filtrationfiltered
- washwashed with tert-butyl methyl ether (20 mL×2)
- concentrationThe combined filtrate was concentrated under reduced pressure
- customthe residue was purified by silica gel column chromatography with elution system B
Sources & evidence
- ORD record
- ord-4fa7ae7bf8d34a3d9a953d8922961968
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09139548B2
Reaction notes
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