1,3-Dibromopropane → (5-Bromo-2-methylpentane-2-sulfonyl)benzene
Reaction equation
C([Li])CCC.[CH:6]([S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:11])=[O:10])([CH3:8])[CH3:7].[Br:18][CH2:19][CH2:20][CH2:21]Br>O1CCCC1>[Br:18][CH2:19][CH2:20][CH2:21][C:6]([CH3:8])([S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:10])=[O:11])[CH3:7]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of n-butyllithium in cyclohexanes (1.82M, 18 ml, 32.8 mmol) was added dropwise to a stirred solution of phenyl i-propyl sulphone (5.55 g, 30.1 mmol) in tetrahydrofuran (60 ml) at −78° C. The mixture was stirred for 30 min. and 1,3-dibromopropane (6 ml, 58.7 mmol) was added via syringe over 30 seconds. The mixture was allowed to warm to 0° C. over 3 hours, then quenched with satd. aqueous NH4Cl and extracted into 1:1 mixture of i-hexane-diethyl ether. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified on silica (i-hexane-diethyl ether) to give the title product (5.7 g, 62%) as a white solid.
Workup
- customquenched with satd
- extractionaqueous NH4Cl and extracted into 1:1 mixture of i-hexane-diethyl ether
- dry with materialThe combined organic extracts were dried (Na2SO4)
- concentrationconcentrated
- customThe residue was purified on silica (i-hexane-diethyl ether)
Sources & evidence
- ORD record
- ord-438e0c525ef3423a9b3a73badcce598d
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07101892B2
Reaction notes
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