Water → (Benzyloxy)ethyl 4-bromobenzenesulfonate

HRID 1826474Notes

Reaction equation

HRID 1826474 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:12]([O:19][CH2:20][CH2:21][OH:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.O>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:22][CH2:21][CH2:20][O:19][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7396p-Bromobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 121412-(Benzyloxy) ethanol

Product 1

HCID 20702450(Benzyloxy)ethyl 4-bromobenzenesulfonateYield 94.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-bromobenzenesulfonyl chloride (5.5 g, 21.7 mmol) dissolved in dichloromethane (15 ml) was added dropwise to a solution of 2-benzyloxyethanol (3.0 g, 19.7 mmol) in triethylamine (3 g, 29.6 mmol) at 0° C. under nitrogen. The resultant mixture was stirred for 16 h at room temperature. To the reaction mixture was added water (3 ml) and then the combined mixture was poured onto water (100 ml) and the product was extracted with dichloromethane. The organic layer was washed repeatedly with water and then saturated aqueous sodium hydrogen carbonate solution, before drying (Na2SO4) and concentrating in vacuo to give the title compound as a white solid (6.9 g, 94%).

Workup

  1. additionthe combined mixture was poured onto water (100 ml)
  2. extractionthe product was extracted with dichloromethane
  3. washThe organic layer was washed repeatedly with water
  4. dry with materialsaturated aqueous sodium hydrogen carbonate solution, before drying (Na2SO4)
  5. concentrationconcentrating in vacuo

Sources & evidence

ORD record
ord-4706308a821841348d32be75e4590708
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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