1,4-Dibromobenzene → HCID 131733144, compound
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.[Li][CH2:10][CH2:11][CH2:12][CH3:13].C1(/C=[N:21]/[S@:22]([C:24]([CH3:27])([CH3:26])[CH3:25])=[O:23])CCCCC1.[CH2:28]1[CH2:32]OC[CH2:29]1>>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([CH:10]([CH2:25][C:24]([CH3:27])([S@@:22]([NH2:21])=[O:23])[CH3:26])[CH:11]2[CH2:32][CH2:28][CH2:29][CH2:13][CH2:12]2)=[CH:3][CH:4]=1Participants
Conditions
- Temperature
- -70 °C
Procedure
1,4-dibromobenzene (20 g, 84.7 mmol) was dissolved in anhydrous THF (300 ml) and the resulting mixture was then cooled to −70° C. Then BuLi (34 mL, 84.6 mmol) was added dropwise at that temperature. The mixture was stirred at −70° C. for 1 hour, then (S,E)-N-(cyclohexylmethylene)-2-methylpropane-2-sulfinamide, 27-a, (14 g, 65 mmol) in anhydrous THF (30 ml) was added dropwise into the mixture at −70° C. The mixture was then stirred overnight from −70° C. to 10° C. The mixture was quenched with saturated NH4Cl followed by extraction with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under vacuum. The residue was purified by column chromatography (petroleum ether/ethyl acetate=30/1) to provide the product, 27-b, (5.4 g, 22.33%). HPLC indicated that the reaction underwent excellent stereoselectivity.
Workup
- stirringThe mixture was then stirred overnight from −70° C. to 10° C
- customThe mixture was quenched with saturated NH4Cl
- extractionfollowed by extraction with ethyl acetate
- dry with materialThe organic layer was dried over sodium sulfate
- concentrationconcentrated under vacuum
- customThe residue was purified by column chromatography (petroleum ether/ethyl acetate=30/1)
Sources & evidence
- ORD record
- ord-40e6d54530ee4527b8485efaecf10aba
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079930B2
Reaction notes
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