p-Bromobenzenesulfonyl chloride → 2-Cyclohexyloxyethyl 4-bromobenzenesulfonate

HRID 428959Notes

Reaction equation

HRID 428959 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 resulting 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%).

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-7370641287b04fc587e77c24f21f3811
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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