4-Toluenesulfonyl chloride → (+)-3-Acetoxy-2-(4-bromophenyl)propyl 4-methyl-benzenesulfonate

HRID 515459Notes

Reaction equation

HRID 515459 reaction equation
[C:1]([O:4][CH2:5][CH:6]([C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=1)[CH2:7][OH:8])(=[O:3])[CH3:2].C(N(CC)CC)C.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>ClCCl.CN(C)C1C=CN=CC=1>[CH3:33][C:23]1[CH:28]=[CH:27][C:26]([S:29]([O:8][CH2:7][CH:6]([C:9]2[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=2)[CH2:5][O:4][C:1](=[O:3])[CH3:2])(=[O:31])=[O:30])=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 66718437(-)-2-(4-Bromophenyl)-3-hydroxypropyl acetate

Product 1

HCID 86664263(+)-3-Acetoxy-2-(4-bromophenyl)propyl 4-methyl-benzenesulfonateYield 90.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (−)-2-(4-bromophenyl)-3-hydroxypropyl acetate (5.88 g, 21.5 mmol) in dichloromethane (100 ml) was added triethylamine (5.45 g, 53.8 mmol), p-toluenesulfonyl chloride (4.93 g, 25.8 mmol) and 4-dimethylaminopyridine (0.263 g, 2.15 mmol) at 0° C. The mixture was stirred at room temperature for 2 hours and partitioned between saturated ammonium chloride solution and dichloromethane. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate=4/1) to afford (+)-3-acetoxy-2-(4-bromophenyl)propyl 4-methyl-benzenesulfonate as colorless oil (8.32 g, 90%). [α]D=+1.63 (C=0.5, CHCl3).

Workup

  1. custompartitioned between saturated ammonium chloride solution and dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-80bedcfc2f614c2b98cd9a278d52005b
Source dataset
uspto-grants-2015_08
Patent number
US09108957B2

Reaction notes

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