p-Bromobenzenesulfonyl chloride → 2-Cyclohexyloxyethyl 4-bromobenzenesulfonate

HRID 397722Notes

Reaction equation

HRID 397722 reaction equation
[CH:1]1([O:7][CH:8](C)[CH2:9][OH:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1>C(N(CC)CC)C.ClCCl>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([O:10][CH2:9][CH2:8][O:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 152185732-Cyclohexyloxy-1-propanol

Product 1

HCID 221413132-Cyclohexyloxyethyl 4-bromobenzenesulfonateYield 80%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 2-cyclohexyloxy-1-propanol (4.0 g, 28 mmol) in triethylamine (5.8 ml) and dichloromethane (250 ml) was added 4-bromobenzenesulfonyl chloride (7.87 g, 31 mmol) at 0° C. under nitrogen, and the resultant mixture was stirred for 16 h at room temperature. The reaction mixture was washed with saturated aqueous sodium hydrogen carbonate solution, water and brine (100 ml each), dried (MgSO4) and concentrated in vacuo to give the crude product. This was purified by silica (200 g) column chromatography using a gradient elution of hexane:ethyl acetate (6:1 to 1:1) to give the title compound as a white crystalline solid (8.0 g, 80% yield).

Workup

  1. washThe reaction mixture was washed with saturated aqueous sodium hydrogen carbonate solution, water and brine (100 ml each)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customto give the crude product
  5. customThis was purified by silica (200 g) column chromatography
  6. washa gradient elution of hexane:ethyl acetate (6:1 to 1:1)

Sources & evidence

ORD record
ord-464a3d344d654b9ba1c60005faac4b41
Source dataset
uspto-grants-2003_08
Patent number
US06610711B2

Reaction notes

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