N-bromobutanimide → (5-(Bromomethyl)-2-chlorophenoxy)(tert-butyl)dimethylsilane
Reaction equation
[C:1]([Si:5]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:10]=1[Cl:16])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:17][CH2:15][C:13]1[CH:12]=[CH:11][C:10]([Cl:16])=[C:9]([CH:14]=1)[O:8][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:7])[CH3:6]Participants
Conditions
- Temperature
- 85 °C
Procedure
A solution containing tert-butyl(2-chloro-5-methylphenoxy)dimethylsilane 80 (6.15 g, 24 mmol), N-bromosuccinimide (4.7 g, 26 mmol), and benzoyl peroxide (0.058 g, 0.24 mmol) in 40 mL of dry CHCl3 was purged with N2 and heated to 85° C. The reaction was exposed to a 60 W lamp and was stirred at reflux for 4 h. The lamp was removed and the reaction was cooled to room temperature. The solution was concentrated and was redissolved in ether. The mixture was filtered and then concentrated again. The crude material was purified by silica gel chromatography using a 5% to 20% gradient of EtOAc in hexanes as the eluant. The desired fractions were combined and concentrated to give (5-(bromomethyl)-2-chlorophenoxy)(tert-butyl)dimethylsilane 81 (2.7 g, 34% yield). The product was carried forth to the next step as is.
Workup
- customwas purged with N2
- temperatureat reflux for 4 h
- customThe lamp was removed
- temperaturethe reaction was cooled to room temperature
- concentrationThe solution was concentrated
- dissolutionwas redissolved in ether
- filtrationThe mixture was filtered
- concentrationconcentrated again
- customThe crude material was purified by silica gel chromatography
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-660a01eeb39c4108b2878d66517f8590
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08349831B2
Reaction notes
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