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p-Bromobenzenesulfonyl chloride → 3-Cyclopentylpropyl 4-bromobenzenesulfonate

HRID 397715
Notes
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Reaction equation

HRID 397715 reaction equation
[CH:1]1([CH2:6][CH2:7][CH2:8][OH:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[Br:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>ClCCl.Cl>[Br:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([O:9][CH2:8][CH2:7][CH2:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)(=[O:26])=[O:25])=[CH:20][CH:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 69842Cyclopentanepropanol

Product 1

HCID 230009943-Cyclopentylpropyl 4-bromobenzenesulfonateYield 83.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent
HCID 6344
Dichloromethane
Solvent

Procedure

To a solution of 3-cyclopentyl-1-propanol (2.0 g, 15.6 mmol) in triethylamine (3.25 ml, 23.4 mmol) and dichloromethane (50 ml) was added 4-bromobenzenesulfonyl chloride (4.4 g, 17.6 mmol). The solution was stirred for 16 h, diluted with 2 N aqueous hydrochloric acid (100 ml) and extracted with dichloromethane (100 ml). The extract was washed with saturated aqueous sodium hydrogen carbonate solution (100 ml) and brine (100 ml), dried (MgSO4) and concentrated in vacuo to give the title compound as a white crystalline solid (4.50 g, 80%).

Workup

  1. extractionextracted with dichloromethane (100 ml)
  2. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution (100 ml) and brine (100 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-71e6cd67d026411793d852f7d654c0d8
Source dataset
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06610711B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes